<?xml version="1.0" encoding="UTF-8"?>

<!--XBRL Document Created with Wdesk from Workiva-->
<!--Copyright 2023 Workiva-->
<!--r:e05e9336-2827-4bfc-b42f-2fc17f79ca39,g:3ce5a072-6244-4eb6-9298-8a839b6bcbed-->
<link:linkbase xmlns:link="http://www.xbrl.org/2003/linkbase" xmlns:xlink="http://www.w3.org/1999/xlink" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" xsi:schemaLocation="http://www.xbrl.org/2003/linkbase http://www.xbrl.org/2003/xbrl-linkbase-2003-12-31.xsd">
  <link:roleRef roleURI="http://www.cantaloupe.com/role/CondensedConsolidatedBalanceSheets" xlink:type="simple" xlink:href="ctlp-20230331.xsd#CondensedConsolidatedBalanceSheets"/>
  <link:calculationLink xlink:role="http://www.cantaloupe.com/role/CondensedConsolidatedBalanceSheets" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilitiesAndStockholdersEquity_da6a7e7e-67fa-4ed6-8774-42788c6fefea" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LiabilitiesAndStockholdersEquity"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_Liabilities_861e3dc4-18da-4b81-a86c-5c2d122044a8" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_Liabilities"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_LiabilitiesAndStockholdersEquity_da6a7e7e-67fa-4ed6-8774-42788c6fefea" xlink:to="loc_us-gaap_Liabilities_861e3dc4-18da-4b81-a86c-5c2d122044a8" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommitmentsAndContingencies_95b8af4d-dcfd-48bb-bc8e-5dbd8d8801f3" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_CommitmentsAndContingencies"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_LiabilitiesAndStockholdersEquity_da6a7e7e-67fa-4ed6-8774-42788c6fefea" xlink:to="loc_us-gaap_CommitmentsAndContingencies_95b8af4d-dcfd-48bb-bc8e-5dbd8d8801f3" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StockholdersEquity_2435ac26-eb46-43cd-96a8-17a5e76577d5" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_StockholdersEquity"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_LiabilitiesAndStockholdersEquity_da6a7e7e-67fa-4ed6-8774-42788c6fefea" xlink:to="loc_us-gaap_StockholdersEquity_2435ac26-eb46-43cd-96a8-17a5e76577d5" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_TemporaryEquityCarryingAmountAttributableToParent_e667ec74-b91c-4add-82ba-27881265973a" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_TemporaryEquityCarryingAmountAttributableToParent"/>
    <link:calculationArc order="4" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_LiabilitiesAndStockholdersEquity_da6a7e7e-67fa-4ed6-8774-42788c6fefea" xlink:to="loc_us-gaap_TemporaryEquityCarryingAmountAttributableToParent_e667ec74-b91c-4add-82ba-27881265973a" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AssetsNoncurrent_b31b5919-d9e4-4c5f-9d4d-05642a5a0a3e" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AssetsNoncurrent"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NotesAndLoansReceivableNetNoncurrent_281c2218-0e13-4873-a2e3-6567fb33a9da" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_NotesAndLoansReceivableNetNoncurrent"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_AssetsNoncurrent_b31b5919-d9e4-4c5f-9d4d-05642a5a0a3e" xlink:to="loc_us-gaap_NotesAndLoansReceivableNetNoncurrent_281c2218-0e13-4873-a2e3-6567fb33a9da" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherAssetsNoncurrent_c70647c5-9fe3-478b-aaed-8c030e3f0c8f" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_OtherAssetsNoncurrent"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_AssetsNoncurrent_b31b5919-d9e4-4c5f-9d4d-05642a5a0a3e" xlink:to="loc_us-gaap_OtherAssetsNoncurrent_c70647c5-9fe3-478b-aaed-8c030e3f0c8f" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PropertyPlantAndEquipmentNet_8160113a-6641-4cf3-b766-e50db760585a" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PropertyPlantAndEquipmentNet"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_AssetsNoncurrent_b31b5919-d9e4-4c5f-9d4d-05642a5a0a3e" xlink:to="loc_us-gaap_PropertyPlantAndEquipmentNet_8160113a-6641-4cf3-b766-e50db760585a" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OperatingLeaseRightOfUseAsset_d4c4a037-05e8-4a86-bf00-1e597815d6ca" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_OperatingLeaseRightOfUseAsset"/>
    <link:calculationArc order="4" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_AssetsNoncurrent_b31b5919-d9e4-4c5f-9d4d-05642a5a0a3e" xlink:to="loc_us-gaap_OperatingLeaseRightOfUseAsset_d4c4a037-05e8-4a86-bf00-1e597815d6ca" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IntangibleAssetsNetExcludingGoodwill_d058c4b3-a7bb-472f-9244-f4a52bec750a" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_IntangibleAssetsNetExcludingGoodwill"/>
    <link:calculationArc order="5" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_AssetsNoncurrent_b31b5919-d9e4-4c5f-9d4d-05642a5a0a3e" xlink:to="loc_us-gaap_IntangibleAssetsNetExcludingGoodwill_d058c4b3-a7bb-472f-9244-f4a52bec750a" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_Goodwill_89b3f183-64c0-4f75-96be-6f84e68313b6" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_Goodwill"/>
    <link:calculationArc order="6" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_AssetsNoncurrent_b31b5919-d9e4-4c5f-9d4d-05642a5a0a3e" xlink:to="loc_us-gaap_Goodwill_89b3f183-64c0-4f75-96be-6f84e68313b6" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AssetsCurrent_960a0a2c-98e5-40b3-ac94-a1c0ec836eb2" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AssetsCurrent"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CashAndCashEquivalentsAtCarryingValue_9900eb4e-9161-4176-8f66-c7facac97083" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_CashAndCashEquivalentsAtCarryingValue"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_AssetsCurrent_960a0a2c-98e5-40b3-ac94-a1c0ec836eb2" xlink:to="loc_us-gaap_CashAndCashEquivalentsAtCarryingValue_9900eb4e-9161-4176-8f66-c7facac97083" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AccountsReceivableNetCurrent_91c03047-2d66-4d10-8d6c-a763c40e6cbf" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AccountsReceivableNetCurrent"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_AssetsCurrent_960a0a2c-98e5-40b3-ac94-a1c0ec836eb2" xlink:to="loc_us-gaap_AccountsReceivableNetCurrent_91c03047-2d66-4d10-8d6c-a763c40e6cbf" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NotesAndLoansReceivableNetCurrent_8b79c458-de83-49cf-b448-17e17285b026" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_NotesAndLoansReceivableNetCurrent"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_AssetsCurrent_960a0a2c-98e5-40b3-ac94-a1c0ec836eb2" xlink:to="loc_us-gaap_NotesAndLoansReceivableNetCurrent_8b79c458-de83-49cf-b448-17e17285b026" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InventoryNet_b6c2db70-2fa5-47c0-89ea-b09c48beb8fd" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_InventoryNet"/>
    <link:calculationArc order="4" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_AssetsCurrent_960a0a2c-98e5-40b3-ac94-a1c0ec836eb2" xlink:to="loc_us-gaap_InventoryNet_b6c2db70-2fa5-47c0-89ea-b09c48beb8fd" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PrepaidExpenseAndOtherAssetsCurrent_93ea7088-c525-4a74-9d9a-b78d56ec8249" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PrepaidExpenseAndOtherAssetsCurrent"/>
    <link:calculationArc order="5" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_AssetsCurrent_960a0a2c-98e5-40b3-ac94-a1c0ec836eb2" xlink:to="loc_us-gaap_PrepaidExpenseAndOtherAssetsCurrent_93ea7088-c525-4a74-9d9a-b78d56ec8249" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StockholdersEquity_b0425411-582a-48d6-b5b9-2d21f28e0755" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_StockholdersEquity"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommonStockValue_b568e1b3-70de-4ea4-9230-7651286fff57" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_CommonStockValue"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_StockholdersEquity_b0425411-582a-48d6-b5b9-2d21f28e0755" xlink:to="loc_us-gaap_CommonStockValue_b568e1b3-70de-4ea4-9230-7651286fff57" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RetainedEarningsAccumulatedDeficit_afc67e55-4dfc-4918-9892-9d8f6f75e632" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_RetainedEarningsAccumulatedDeficit"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_StockholdersEquity_b0425411-582a-48d6-b5b9-2d21f28e0755" xlink:to="loc_us-gaap_RetainedEarningsAccumulatedDeficit_afc67e55-4dfc-4918-9892-9d8f6f75e632" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_Assets_a5f6eb48-ba1a-4ea2-8f89-d8e5433f5cf1" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_Assets"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AssetsCurrent_3ccfe2fd-cfe1-443e-8dac-b0490511bd3a" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AssetsCurrent"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_Assets_a5f6eb48-ba1a-4ea2-8f89-d8e5433f5cf1" xlink:to="loc_us-gaap_AssetsCurrent_3ccfe2fd-cfe1-443e-8dac-b0490511bd3a" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AssetsNoncurrent_00ed2044-73c2-4aef-ac7f-c04c01cbbb03" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AssetsNoncurrent"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_Assets_a5f6eb48-ba1a-4ea2-8f89-d8e5433f5cf1" xlink:to="loc_us-gaap_AssetsNoncurrent_00ed2044-73c2-4aef-ac7f-c04c01cbbb03" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilitiesNoncurrent_797151e2-624c-44d6-9b61-065e76a30fb7" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LiabilitiesNoncurrent"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DeferredIncomeTaxLiabilitiesNet_53bce26b-4d3c-44d0-b887-7d9c1fe81605" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DeferredIncomeTaxLiabilitiesNet"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_LiabilitiesNoncurrent_797151e2-624c-44d6-9b61-065e76a30fb7" xlink:to="loc_us-gaap_DeferredIncomeTaxLiabilitiesNet_53bce26b-4d3c-44d0-b887-7d9c1fe81605" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LongTermDebtNoncurrent_2a4a4694-a429-407a-9979-6b16a2e63a6c" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LongTermDebtNoncurrent"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_LiabilitiesNoncurrent_797151e2-624c-44d6-9b61-065e76a30fb7" xlink:to="loc_us-gaap_LongTermDebtNoncurrent_2a4a4694-a429-407a-9979-6b16a2e63a6c" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OperatingLeaseLiabilityNoncurrent_9b9265f5-f1f2-46c8-b29c-56b3432423c1" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_OperatingLeaseLiabilityNoncurrent"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_LiabilitiesNoncurrent_797151e2-624c-44d6-9b61-065e76a30fb7" xlink:to="loc_us-gaap_OperatingLeaseLiabilityNoncurrent_9b9265f5-f1f2-46c8-b29c-56b3432423c1" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilitiesCurrent_7388ca80-09eb-452b-9380-19523f7d8aa0" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LiabilitiesCurrent"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AccruedLiabilitiesCurrent_e170ea6e-825a-44bd-8009-08bf80e5f8ac" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AccruedLiabilitiesCurrent"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_LiabilitiesCurrent_7388ca80-09eb-452b-9380-19523f7d8aa0" xlink:to="loc_us-gaap_AccruedLiabilitiesCurrent_e170ea6e-825a-44bd-8009-08bf80e5f8ac" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AccountsPayableCurrent_19a0cd0e-f8bf-41f2-a40a-d271fc6c18fa" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AccountsPayableCurrent"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_LiabilitiesCurrent_7388ca80-09eb-452b-9380-19523f7d8aa0" xlink:to="loc_us-gaap_AccountsPayableCurrent_19a0cd0e-f8bf-41f2-a40a-d271fc6c18fa" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ContractWithCustomerLiabilityCurrent_ec0e22dc-a91f-4c6d-8de5-e1fbd55b3f49" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ContractWithCustomerLiabilityCurrent"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_LiabilitiesCurrent_7388ca80-09eb-452b-9380-19523f7d8aa0" xlink:to="loc_us-gaap_ContractWithCustomerLiabilityCurrent_ec0e22dc-a91f-4c6d-8de5-e1fbd55b3f49" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LongTermDebtCurrent_6e4ebd67-78f7-4f85-b8c4-f4246766e0c4" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LongTermDebtCurrent"/>
    <link:calculationArc order="4" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_LiabilitiesCurrent_7388ca80-09eb-452b-9380-19523f7d8aa0" xlink:to="loc_us-gaap_LongTermDebtCurrent_6e4ebd67-78f7-4f85-b8c4-f4246766e0c4" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_Liabilities_e7990e79-c367-4fdd-869f-05acdd48bbae" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_Liabilities"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilitiesCurrent_0080affa-2ab0-4834-92fd-c43054cc044a" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LiabilitiesCurrent"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_Liabilities_e7990e79-c367-4fdd-869f-05acdd48bbae" xlink:to="loc_us-gaap_LiabilitiesCurrent_0080affa-2ab0-4834-92fd-c43054cc044a" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilitiesNoncurrent_7d27c2f7-dfeb-4295-a9d8-e5f7617042eb" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LiabilitiesNoncurrent"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_Liabilities_e7990e79-c367-4fdd-869f-05acdd48bbae" xlink:to="loc_us-gaap_LiabilitiesNoncurrent_7d27c2f7-dfeb-4295-a9d8-e5f7617042eb" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://www.cantaloupe.com/role/CondensedConsolidatedStatementsofOperations" xlink:type="simple" xlink:href="ctlp-20230331.xsd#CondensedConsolidatedStatementsofOperations"/>
  <link:calculationLink xlink:role="http://www.cantaloupe.com/role/CondensedConsolidatedStatementsofOperations" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetIncomeLossAvailableToCommonStockholdersBasic_3bc5f7a8-53ef-4fa8-a50a-a1f511696f06" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_NetIncomeLossAvailableToCommonStockholdersBasic"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetIncomeLoss_942c6805-137f-4057-8ed3-12cd9f4b6a98" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_NetIncomeLoss"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetIncomeLossAvailableToCommonStockholdersBasic_3bc5f7a8-53ef-4fa8-a50a-a1f511696f06" xlink:to="loc_us-gaap_NetIncomeLoss_942c6805-137f-4057-8ed3-12cd9f4b6a98" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PreferredStockDividendsIncomeStatementImpact_a3d85a3e-8d41-423e-b983-bdf732e2f870" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PreferredStockDividendsIncomeStatementImpact"/>
    <link:calculationArc order="2" weight="-1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetIncomeLossAvailableToCommonStockholdersBasic_3bc5f7a8-53ef-4fa8-a50a-a1f511696f06" xlink:to="loc_us-gaap_PreferredStockDividendsIncomeStatementImpact_a3d85a3e-8d41-423e-b983-bdf732e2f870" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OperatingIncomeLoss_b301c755-c562-40dd-a956-4222e351451d" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_OperatingIncomeLoss"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GrossProfit_5494cb1c-5ee3-4df3-a992-f47b445947d4" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_GrossProfit"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_OperatingIncomeLoss_b301c755-c562-40dd-a956-4222e351451d" xlink:to="loc_us-gaap_GrossProfit_5494cb1c-5ee3-4df3-a992-f47b445947d4" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OperatingExpenses_03fc5aa9-835a-4864-91f6-031404714f23" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_OperatingExpenses"/>
    <link:calculationArc order="2" weight="-1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_OperatingIncomeLoss_b301c755-c562-40dd-a956-4222e351451d" xlink:to="loc_us-gaap_OperatingExpenses_03fc5aa9-835a-4864-91f6-031404714f23" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OperatingExpenses_fe7739ff-d002-4cbc-b6eb-8f0efd8575ad" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_OperatingExpenses"/>
    <link:loc xlink:type="locator" xlink:label="loc_ctlp_ProfessionalExpensesProceeds_5e95228c-1f01-4709-a7f9-c1e03de026c8" xlink:href="ctlp-20230331.xsd#ctlp_ProfessionalExpensesProceeds"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_OperatingExpenses_fe7739ff-d002-4cbc-b6eb-8f0efd8575ad" xlink:to="loc_ctlp_ProfessionalExpensesProceeds_5e95228c-1f01-4709-a7f9-c1e03de026c8" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DepreciationAndAmortization_f2bc9d08-65cd-45c3-a381-e19644f82f8a" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DepreciationAndAmortization"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_OperatingExpenses_fe7739ff-d002-4cbc-b6eb-8f0efd8575ad" xlink:to="loc_us-gaap_DepreciationAndAmortization_f2bc9d08-65cd-45c3-a381-e19644f82f8a" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_ctlp_BusinessCombinationAcquisitionAndIntegrationRelatedCosts_fd3c1fc0-532a-4de5-9962-24b791086060" xlink:href="ctlp-20230331.xsd#ctlp_BusinessCombinationAcquisitionAndIntegrationRelatedCosts"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_OperatingExpenses_fe7739ff-d002-4cbc-b6eb-8f0efd8575ad" xlink:to="loc_ctlp_BusinessCombinationAcquisitionAndIntegrationRelatedCosts_fd3c1fc0-532a-4de5-9962-24b791086060" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InformationTechnologyAndDataProcessing_574153c9-1eca-4435-a295-a040fd13b900" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_InformationTechnologyAndDataProcessing"/>
    <link:calculationArc order="4" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_OperatingExpenses_fe7739ff-d002-4cbc-b6eb-8f0efd8575ad" xlink:to="loc_us-gaap_InformationTechnologyAndDataProcessing_574153c9-1eca-4435-a295-a040fd13b900" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GeneralAndAdministrativeExpense_bc66b2f0-dead-4f4d-a928-18cebb8c60f3" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_GeneralAndAdministrativeExpense"/>
    <link:calculationArc order="5" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_OperatingExpenses_fe7739ff-d002-4cbc-b6eb-8f0efd8575ad" xlink:to="loc_us-gaap_GeneralAndAdministrativeExpense_bc66b2f0-dead-4f4d-a928-18cebb8c60f3" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SellingAndMarketingExpense_2f1fb4b0-d284-42bb-9278-5e6ea510080d" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_SellingAndMarketingExpense"/>
    <link:calculationArc order="6" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_OperatingExpenses_fe7739ff-d002-4cbc-b6eb-8f0efd8575ad" xlink:to="loc_us-gaap_SellingAndMarketingExpense_2f1fb4b0-d284-42bb-9278-5e6ea510080d" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NonoperatingIncomeExpense_b9a44d92-c1fd-4d07-9b75-d1d76cb9f760" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_NonoperatingIncomeExpense"/>
    <link:loc xlink:type="locator" xlink:label="loc_ctlp_LessorOperatingLeaseInterestIncomeNonoperating_96f2ce32-d86d-414c-a7f8-e7ad9bfac500" xlink:href="ctlp-20230331.xsd#ctlp_LessorOperatingLeaseInterestIncomeNonoperating"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NonoperatingIncomeExpense_b9a44d92-c1fd-4d07-9b75-d1d76cb9f760" xlink:to="loc_ctlp_LessorOperatingLeaseInterestIncomeNonoperating_96f2ce32-d86d-414c-a7f8-e7ad9bfac500" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_ctlp_InterestExpenseReversalOfExpense_03a748d5-bd1a-4d92-9d1b-2a97ed801baa" xlink:href="ctlp-20230331.xsd#ctlp_InterestExpenseReversalOfExpense"/>
    <link:calculationArc order="2" weight="-1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NonoperatingIncomeExpense_b9a44d92-c1fd-4d07-9b75-d1d76cb9f760" xlink:to="loc_ctlp_InterestExpenseReversalOfExpense_03a748d5-bd1a-4d92-9d1b-2a97ed801baa" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GainLossOnDerivativeInstrumentsNetPretax_1e542b73-4504-4edf-9f1c-37825ca74d80" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_GainLossOnDerivativeInstrumentsNetPretax"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NonoperatingIncomeExpense_b9a44d92-c1fd-4d07-9b75-d1d76cb9f760" xlink:to="loc_us-gaap_GainLossOnDerivativeInstrumentsNetPretax_1e542b73-4504-4edf-9f1c-37825ca74d80" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GrossProfit_2a5249bd-bd15-4e9d-bb29-6599d943aa8b" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_GrossProfit"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RevenueFromContractWithCustomerExcludingAssessedTax_a6bbd9fb-2a93-4754-bee6-494acd8c0145" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_RevenueFromContractWithCustomerExcludingAssessedTax"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_GrossProfit_2a5249bd-bd15-4e9d-bb29-6599d943aa8b" xlink:to="loc_us-gaap_RevenueFromContractWithCustomerExcludingAssessedTax_a6bbd9fb-2a93-4754-bee6-494acd8c0145" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CostOfRevenue_5be61c6e-87e5-4691-9525-6304e517ba3b" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_CostOfRevenue"/>
    <link:calculationArc order="2" weight="-1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_GrossProfit_2a5249bd-bd15-4e9d-bb29-6599d943aa8b" xlink:to="loc_us-gaap_CostOfRevenue_5be61c6e-87e5-4691-9525-6304e517ba3b" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetIncomeLoss_0df672cd-a95d-44f5-95bb-067df8dde80c" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_NetIncomeLoss"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest_6464812d-f4f3-45dd-a9d6-06e1d3e68c78" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetIncomeLoss_0df672cd-a95d-44f5-95bb-067df8dde80c" xlink:to="loc_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest_6464812d-f4f3-45dd-a9d6-06e1d3e68c78" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeTaxExpenseBenefit_911386a1-69ba-423b-b1f0-cec38ff194b8" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_IncomeTaxExpenseBenefit"/>
    <link:calculationArc order="2" weight="-1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetIncomeLoss_0df672cd-a95d-44f5-95bb-067df8dde80c" xlink:to="loc_us-gaap_IncomeTaxExpenseBenefit_911386a1-69ba-423b-b1f0-cec38ff194b8" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest_7f162e6c-e20a-4e15-acb2-fff460ae7b1b" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OperatingIncomeLoss_56a33aba-9132-4a5c-b457-844874b15d9f" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_OperatingIncomeLoss"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest_7f162e6c-e20a-4e15-acb2-fff460ae7b1b" xlink:to="loc_us-gaap_OperatingIncomeLoss_56a33aba-9132-4a5c-b457-844874b15d9f" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NonoperatingIncomeExpense_2bae52b4-1965-4378-813e-83fb6a683774" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_NonoperatingIncomeExpense"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest_7f162e6c-e20a-4e15-acb2-fff460ae7b1b" xlink:to="loc_us-gaap_NonoperatingIncomeExpense_2bae52b4-1965-4378-813e-83fb6a683774" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://www.cantaloupe.com/role/CondensedConsolidatedStatementsofCashFlows" xlink:type="simple" xlink:href="ctlp-20230331.xsd#CondensedConsolidatedStatementsofCashFlows"/>
  <link:calculationLink xlink:role="http://www.cantaloupe.com/role/CondensedConsolidatedStatementsofCashFlows" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInFinancingActivities_d816b0ac-5bad-4e5a-a8b6-65ab52804762" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_NetCashProvidedByUsedInFinancingActivities"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromIssuanceOfOtherLongTermDebt_a4a980eb-c492-4668-a0a7-cb66cb7881db" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ProceedsFromIssuanceOfOtherLongTermDebt"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInFinancingActivities_d816b0ac-5bad-4e5a-a8b6-65ab52804762" xlink:to="loc_us-gaap_ProceedsFromIssuanceOfOtherLongTermDebt_a4a980eb-c492-4668-a0a7-cb66cb7881db" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromStockOptionsExercised_1225c974-bd14-4b43-a830-1fea1f3eefd1" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ProceedsFromStockOptionsExercised"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInFinancingActivities_d816b0ac-5bad-4e5a-a8b6-65ab52804762" xlink:to="loc_us-gaap_ProceedsFromStockOptionsExercised_1225c974-bd14-4b43-a830-1fea1f3eefd1" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentForContingentConsiderationLiabilityFinancingActivities_dc8fdf84-3ec1-4ea4-bff6-025b5c6a9313" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PaymentForContingentConsiderationLiabilityFinancingActivities"/>
    <link:calculationArc order="3" weight="-1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInFinancingActivities_d816b0ac-5bad-4e5a-a8b6-65ab52804762" xlink:to="loc_us-gaap_PaymentForContingentConsiderationLiabilityFinancingActivities_dc8fdf84-3ec1-4ea4-bff6-025b5c6a9313" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsOfDebtIssuanceCosts_a1ce7729-9421-436c-829f-0228c3a7926b" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PaymentsOfDebtIssuanceCosts"/>
    <link:calculationArc order="4" weight="-1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInFinancingActivities_d816b0ac-5bad-4e5a-a8b6-65ab52804762" xlink:to="loc_us-gaap_PaymentsOfDebtIssuanceCosts_a1ce7729-9421-436c-829f-0228c3a7926b" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RepaymentsOfOtherLongTermDebt_d5e8247d-b78f-4956-827b-4feb34efa215" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_RepaymentsOfOtherLongTermDebt"/>
    <link:calculationArc order="5" weight="-1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInFinancingActivities_d816b0ac-5bad-4e5a-a8b6-65ab52804762" xlink:to="loc_us-gaap_RepaymentsOfOtherLongTermDebt_d5e8247d-b78f-4956-827b-4feb34efa215" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsForRepurchaseOfPreferredStockAndPreferenceStock_44367f1e-2ef3-4eff-a2f0-0c5cf2945005" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PaymentsForRepurchaseOfPreferredStockAndPreferenceStock"/>
    <link:calculationArc order="6" weight="-1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInFinancingActivities_d816b0ac-5bad-4e5a-a8b6-65ab52804762" xlink:to="loc_us-gaap_PaymentsForRepurchaseOfPreferredStockAndPreferenceStock_44367f1e-2ef3-4eff-a2f0-0c5cf2945005" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffect_cc08f4fd-914b-42af-9240-e86b06fe171d" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffect"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_3fc7f3ac-7d49-4957-9a98-90fb37fbcc86" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_NetCashProvidedByUsedInOperatingActivities"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffect_cc08f4fd-914b-42af-9240-e86b06fe171d" xlink:to="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_3fc7f3ac-7d49-4957-9a98-90fb37fbcc86" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInInvestingActivities_ea7d5b11-898f-4956-b512-c8baeaa56801" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_NetCashProvidedByUsedInInvestingActivities"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffect_cc08f4fd-914b-42af-9240-e86b06fe171d" xlink:to="loc_us-gaap_NetCashProvidedByUsedInInvestingActivities_ea7d5b11-898f-4956-b512-c8baeaa56801" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInFinancingActivities_c73c899e-2a93-4825-9a96-c1ab73af0541" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_NetCashProvidedByUsedInFinancingActivities"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffect_cc08f4fd-914b-42af-9240-e86b06fe171d" xlink:to="loc_us-gaap_NetCashProvidedByUsedInFinancingActivities_c73c899e-2a93-4825-9a96-c1ab73af0541" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_43569aa4-1fba-4213-8283-90f43e2da6d1" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_NetCashProvidedByUsedInOperatingActivities"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInFinanceReceivables_9ac0678a-d0a9-48a0-8191-66c44d79d47f" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_IncreaseDecreaseInFinanceReceivables"/>
    <link:calculationArc order="1" weight="-1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_43569aa4-1fba-4213-8283-90f43e2da6d1" xlink:to="loc_us-gaap_IncreaseDecreaseInFinanceReceivables_9ac0678a-d0a9-48a0-8191-66c44d79d47f" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_ctlp_IncreaseDecreaseInOperatingLeaseLiabilities_7ab59066-29c8-4873-8542-9bcde21cce6b" xlink:href="ctlp-20230331.xsd#ctlp_IncreaseDecreaseInOperatingLeaseLiabilities"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_43569aa4-1fba-4213-8283-90f43e2da6d1" xlink:to="loc_ctlp_IncreaseDecreaseInOperatingLeaseLiabilities_7ab59066-29c8-4873-8542-9bcde21cce6b" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInPrepaidDeferredExpenseAndOtherAssets_b3c97fb2-e97b-4ac8-8f07-ced331af5c19" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_IncreaseDecreaseInPrepaidDeferredExpenseAndOtherAssets"/>
    <link:calculationArc order="3" weight="-1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_43569aa4-1fba-4213-8283-90f43e2da6d1" xlink:to="loc_us-gaap_IncreaseDecreaseInPrepaidDeferredExpenseAndOtherAssets_b3c97fb2-e97b-4ac8-8f07-ced331af5c19" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_ctlp_AccountsAndFinancingReceivableCreditLossExpenseReversal_bb0a427f-23cc-4bb7-a642-4230b83f3767" xlink:href="ctlp-20230331.xsd#ctlp_AccountsAndFinancingReceivableCreditLossExpenseReversal"/>
    <link:calculationArc order="4" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_43569aa4-1fba-4213-8283-90f43e2da6d1" xlink:to="loc_ctlp_AccountsAndFinancingReceivableCreditLossExpenseReversal_bb0a427f-23cc-4bb7-a642-4230b83f3767" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EmployeeBenefitsAndShareBasedCompensation_1244b4a9-3fc7-406a-a591-cc5afaae92b1" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_EmployeeBenefitsAndShareBasedCompensation"/>
    <link:calculationArc order="5" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_43569aa4-1fba-4213-8283-90f43e2da6d1" xlink:to="loc_us-gaap_EmployeeBenefitsAndShareBasedCompensation_1244b4a9-3fc7-406a-a591-cc5afaae92b1" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInAccountsPayableAndAccruedLiabilities_aec7d245-2463-4750-a88f-291d0dd92c24" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_IncreaseDecreaseInAccountsPayableAndAccruedLiabilities"/>
    <link:calculationArc order="6" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_43569aa4-1fba-4213-8283-90f43e2da6d1" xlink:to="loc_us-gaap_IncreaseDecreaseInAccountsPayableAndAccruedLiabilities_aec7d245-2463-4750-a88f-291d0dd92c24" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherNoncashIncomeExpense_805ba6cc-8345-4239-9bc3-d47a9f1747e9" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_OtherNoncashIncomeExpense"/>
    <link:calculationArc order="7" weight="-1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_43569aa4-1fba-4213-8283-90f43e2da6d1" xlink:to="loc_us-gaap_OtherNoncashIncomeExpense_805ba6cc-8345-4239-9bc3-d47a9f1747e9" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInInventories_15f88bdf-f982-4488-83e9-0962220f7270" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_IncreaseDecreaseInInventories"/>
    <link:calculationArc order="8" weight="-1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_43569aa4-1fba-4213-8283-90f43e2da6d1" xlink:to="loc_us-gaap_IncreaseDecreaseInInventories_15f88bdf-f982-4488-83e9-0962220f7270" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInAccountsReceivable_b2379512-3934-4bd2-8b69-1c57d025b346" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_IncreaseDecreaseInAccountsReceivable"/>
    <link:calculationArc order="9" weight="-1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_43569aa4-1fba-4213-8283-90f43e2da6d1" xlink:to="loc_us-gaap_IncreaseDecreaseInAccountsReceivable_b2379512-3934-4bd2-8b69-1c57d025b346" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherDepreciationAndAmortization_dacedca7-8e2a-4051-b10b-9417e83bc6cc" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_OtherDepreciationAndAmortization"/>
    <link:calculationArc order="10" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_43569aa4-1fba-4213-8283-90f43e2da6d1" xlink:to="loc_us-gaap_OtherDepreciationAndAmortization_dacedca7-8e2a-4051-b10b-9417e83bc6cc" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInContractWithCustomerLiability_aef3c0e0-12fe-470f-8acc-9ff0f76a7465" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_IncreaseDecreaseInContractWithCustomerLiability"/>
    <link:calculationArc order="11" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_43569aa4-1fba-4213-8283-90f43e2da6d1" xlink:to="loc_us-gaap_IncreaseDecreaseInContractWithCustomerLiability_aef3c0e0-12fe-470f-8acc-9ff0f76a7465" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AmortizationOfDebtDiscountPremium_626fcef9-7dcb-40cf-b851-138962ac0db7" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AmortizationOfDebtDiscountPremium"/>
    <link:calculationArc order="12" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_43569aa4-1fba-4213-8283-90f43e2da6d1" xlink:to="loc_us-gaap_AmortizationOfDebtDiscountPremium_626fcef9-7dcb-40cf-b851-138962ac0db7" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetIncomeLoss_b45ef98f-fbcb-43f2-a661-e6c489d9aea2" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_NetIncomeLoss"/>
    <link:calculationArc order="13" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_43569aa4-1fba-4213-8283-90f43e2da6d1" xlink:to="loc_us-gaap_NetIncomeLoss_b45ef98f-fbcb-43f2-a661-e6c489d9aea2" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_ctlp_DepreciationIncludedInCostOfSalesForRentals_b853705b-5ecf-4a31-a48c-16bf4363cbed" xlink:href="ctlp-20230331.xsd#ctlp_DepreciationIncludedInCostOfSalesForRentals"/>
    <link:calculationArc order="14" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_43569aa4-1fba-4213-8283-90f43e2da6d1" xlink:to="loc_ctlp_DepreciationIncludedInCostOfSalesForRentals_b853705b-5ecf-4a31-a48c-16bf4363cbed" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InventoryWriteDown_21a76870-08b4-48d2-a1da-55d6515e1f2d" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_InventoryWriteDown"/>
    <link:calculationArc order="15" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_43569aa4-1fba-4213-8283-90f43e2da6d1" xlink:to="loc_us-gaap_InventoryWriteDown_21a76870-08b4-48d2-a1da-55d6515e1f2d" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInInvestingActivities_b7c16e57-fdf5-4e52-9b90-bc21eaea34f2" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_NetCashProvidedByUsedInInvestingActivities"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsToAcquirePropertyPlantAndEquipment_8e1a6f05-4267-4765-9703-de23b4ee8b4f" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PaymentsToAcquirePropertyPlantAndEquipment"/>
    <link:calculationArc order="1" weight="-1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInInvestingActivities_b7c16e57-fdf5-4e52-9b90-bc21eaea34f2" xlink:to="loc_us-gaap_PaymentsToAcquirePropertyPlantAndEquipment_8e1a6f05-4267-4765-9703-de23b4ee8b4f" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsToAcquireBusinessesNetOfCashAcquired_d4c42388-9871-4020-847a-6ce0ebfee029" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PaymentsToAcquireBusinessesNetOfCashAcquired"/>
    <link:calculationArc order="2" weight="-1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInInvestingActivities_b7c16e57-fdf5-4e52-9b90-bc21eaea34f2" xlink:to="loc_us-gaap_PaymentsToAcquireBusinessesNetOfCashAcquired_d4c42388-9871-4020-847a-6ce0ebfee029" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://www.cantaloupe.com/role/LEASESAssetsandLiabilitiesDetails" xlink:type="simple" xlink:href="ctlp-20230331.xsd#LEASESAssetsandLiabilitiesDetails"/>
  <link:calculationLink xlink:role="http://www.cantaloupe.com/role/LEASESAssetsandLiabilitiesDetails" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OperatingLeaseLiability_e6337559-3259-4be4-bac6-24d6bf09fcf4" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_OperatingLeaseLiability"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OperatingLeaseLiabilityCurrent_d84a215b-d72d-4162-82f0-c6e8c4ba69c3" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_OperatingLeaseLiabilityCurrent"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_OperatingLeaseLiability_e6337559-3259-4be4-bac6-24d6bf09fcf4" xlink:to="loc_us-gaap_OperatingLeaseLiabilityCurrent_d84a215b-d72d-4162-82f0-c6e8c4ba69c3" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OperatingLeaseLiabilityNoncurrent_312b0586-ae2e-4a05-aa9e-f6f813943a23" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_OperatingLeaseLiabilityNoncurrent"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_OperatingLeaseLiability_e6337559-3259-4be4-bac6-24d6bf09fcf4" xlink:to="loc_us-gaap_OperatingLeaseLiabilityNoncurrent_312b0586-ae2e-4a05-aa9e-f6f813943a23" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://www.cantaloupe.com/role/LEASESMaturitiesofLeaseLiabilitiesDetails" xlink:type="simple" xlink:href="ctlp-20230331.xsd#LEASESMaturitiesofLeaseLiabilitiesDetails"/>
  <link:calculationLink xlink:role="http://www.cantaloupe.com/role/LEASESMaturitiesofLeaseLiabilitiesDetails" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDue_5741ad70-8623-4b09-834b-253f047e4fb7" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LesseeOperatingLeaseLiabilityPaymentsDue"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LesseeOperatingLeaseLiabilityUndiscountedExcessAmount_70c3bcbe-a69a-4e54-a2c4-7df5e81c6ded" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LesseeOperatingLeaseLiabilityUndiscountedExcessAmount"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDue_5741ad70-8623-4b09-834b-253f047e4fb7" xlink:to="loc_us-gaap_LesseeOperatingLeaseLiabilityUndiscountedExcessAmount_70c3bcbe-a69a-4e54-a2c4-7df5e81c6ded" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OperatingLeaseLiability_cea17c5d-6b41-4e83-b638-87832fa5147e" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_OperatingLeaseLiability"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDue_5741ad70-8623-4b09-834b-253f047e4fb7" xlink:to="loc_us-gaap_OperatingLeaseLiability_cea17c5d-6b41-4e83-b638-87832fa5147e" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://www.cantaloupe.com/role/LEASESMaturitiesofLeaseLiabilitiesDetails_1" xlink:type="simple" xlink:href="ctlp-20230331.xsd#LEASESMaturitiesofLeaseLiabilitiesDetails_1"/>
  <link:calculationLink xlink:role="http://www.cantaloupe.com/role/LEASESMaturitiesofLeaseLiabilitiesDetails_1" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDue_1982ea7a-e132-4e6c-a6b7-17777d097158" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LesseeOperatingLeaseLiabilityPaymentsDue"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LesseeOperatingLeaseLiabilityPaymentsRemainderOfFiscalYear_9aa5ccd2-2a6a-4b82-8c61-08f0155b8552" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LesseeOperatingLeaseLiabilityPaymentsRemainderOfFiscalYear"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDue_1982ea7a-e132-4e6c-a6b7-17777d097158" xlink:to="loc_us-gaap_LesseeOperatingLeaseLiabilityPaymentsRemainderOfFiscalYear_9aa5ccd2-2a6a-4b82-8c61-08f0155b8552" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueNextTwelveMonths_78ebf3fa-9df3-437c-9f97-253cbd665e76" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueNextTwelveMonths"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDue_1982ea7a-e132-4e6c-a6b7-17777d097158" xlink:to="loc_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueNextTwelveMonths_78ebf3fa-9df3-437c-9f97-253cbd665e76" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearFour_98103e64-ec98-49ed-aeec-f67b521cb475" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearFour"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDue_1982ea7a-e132-4e6c-a6b7-17777d097158" xlink:to="loc_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearFour_98103e64-ec98-49ed-aeec-f67b521cb475" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearThree_1e944c2a-5f8e-43ff-a095-4c0c16abd1ac" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearThree"/>
    <link:calculationArc order="4" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDue_1982ea7a-e132-4e6c-a6b7-17777d097158" xlink:to="loc_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearThree_1e944c2a-5f8e-43ff-a095-4c0c16abd1ac" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearTwo_35b23f09-a2be-44c3-a7d2-faf3b0c3f788" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearTwo"/>
    <link:calculationArc order="5" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDue_1982ea7a-e132-4e6c-a6b7-17777d097158" xlink:to="loc_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearTwo_35b23f09-a2be-44c3-a7d2-faf3b0c3f788" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_ctlp_LesseeOperatingLeaseLiabilityToBePaidAfterYearFour_c8c0cf67-10e0-4b3b-89e6-0667c01fd22d" xlink:href="ctlp-20230331.xsd#ctlp_LesseeOperatingLeaseLiabilityToBePaidAfterYearFour"/>
    <link:calculationArc order="6" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDue_1982ea7a-e132-4e6c-a6b7-17777d097158" xlink:to="loc_ctlp_LesseeOperatingLeaseLiabilityToBePaidAfterYearFour_c8c0cf67-10e0-4b3b-89e6-0667c01fd22d" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://www.cantaloupe.com/role/LEASESPropertyandEquipmentCostsDetails" xlink:type="simple" xlink:href="ctlp-20230331.xsd#LEASESPropertyandEquipmentCostsDetails"/>
  <link:calculationLink xlink:role="http://www.cantaloupe.com/role/LEASESPropertyandEquipmentCostsDetails" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PropertySubjectToOrAvailableForOperatingLeaseNet_e3657704-4fdc-4ac0-b800-63e1207aa3ad" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PropertySubjectToOrAvailableForOperatingLeaseNet"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PropertySubjectToOrAvailableForOperatingLeaseAccumulatedDepreciation_51aef4d2-56ec-4aec-88a3-862a74bd4ab4" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PropertySubjectToOrAvailableForOperatingLeaseAccumulatedDepreciation"/>
    <link:calculationArc order="1" weight="-1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_PropertySubjectToOrAvailableForOperatingLeaseNet_e3657704-4fdc-4ac0-b800-63e1207aa3ad" xlink:to="loc_us-gaap_PropertySubjectToOrAvailableForOperatingLeaseAccumulatedDepreciation_51aef4d2-56ec-4aec-88a3-862a74bd4ab4" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PropertySubjectToOrAvailableForOperatingLeaseGross_7e7f8e01-5711-43b8-925b-8ce09e697535" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PropertySubjectToOrAvailableForOperatingLeaseGross"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_PropertySubjectToOrAvailableForOperatingLeaseNet_e3657704-4fdc-4ac0-b800-63e1207aa3ad" xlink:to="loc_us-gaap_PropertySubjectToOrAvailableForOperatingLeaseGross_7e7f8e01-5711-43b8-925b-8ce09e697535" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://www.cantaloupe.com/role/ACQUISITIONSummaryofPurchasePriceConsiderationDetails" xlink:type="simple" xlink:href="ctlp-20230331.xsd#ACQUISITIONSummaryofPurchasePriceConsiderationDetails"/>
  <link:calculationLink xlink:role="http://www.cantaloupe.com/role/ACQUISITIONSummaryofPurchasePriceConsiderationDetails" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationConsiderationTransferred1_3427b04b-4145-478a-af4f-6e92d3dbac40" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_BusinessCombinationConsiderationTransferred1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationConsiderationTransferredEquityInterestsIssuedAndIssuable_deb72bca-fbcf-4da5-be75-9e7fb465e26e" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_BusinessCombinationConsiderationTransferredEquityInterestsIssuedAndIssuable"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_BusinessCombinationConsiderationTransferred1_3427b04b-4145-478a-af4f-6e92d3dbac40" xlink:to="loc_us-gaap_BusinessCombinationConsiderationTransferredEquityInterestsIssuedAndIssuable_deb72bca-fbcf-4da5-be75-9e7fb465e26e" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsToAcquireBusinessesNetOfCashAcquired_f3528d7b-08ea-420d-902d-617b68850f5a" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PaymentsToAcquireBusinessesNetOfCashAcquired"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_BusinessCombinationConsiderationTransferred1_3427b04b-4145-478a-af4f-6e92d3dbac40" xlink:to="loc_us-gaap_PaymentsToAcquireBusinessesNetOfCashAcquired_f3528d7b-08ea-420d-902d-617b68850f5a" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://www.cantaloupe.com/role/ACQUISITIONSummaryofAssetsAcquiredandLiabilitiesAssumedDetails" xlink:type="simple" xlink:href="ctlp-20230331.xsd#ACQUISITIONSummaryofAssetsAcquiredandLiabilitiesAssumedDetails"/>
  <link:calculationLink xlink:role="http://www.cantaloupe.com/role/ACQUISITIONSummaryofAssetsAcquiredandLiabilitiesAssumedDetails" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedAssets_91a0aec9-d953-4c79-97b5-dcc481b8d95b" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedAssets"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedInventory_36420bc6-e16f-4e0d-8ae9-07fbb2a902fa" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedInventory"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedAssets_91a0aec9-d953-4c79-97b5-dcc481b8d95b" xlink:to="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedInventory_36420bc6-e16f-4e0d-8ae9-07fbb2a902fa" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedIntangibleAssetsOtherThanGoodwill_955028c5-8524-45fe-b1ea-55a31204cd22" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedIntangibleAssetsOtherThanGoodwill"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedAssets_91a0aec9-d953-4c79-97b5-dcc481b8d95b" xlink:to="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedIntangibleAssetsOtherThanGoodwill_955028c5-8524-45fe-b1ea-55a31204cd22" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedOtherNoncurrentAssets_ba9da7d1-3480-4c06-90f3-e7bff8c6f360" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedOtherNoncurrentAssets"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedAssets_91a0aec9-d953-4c79-97b5-dcc481b8d95b" xlink:to="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedOtherNoncurrentAssets_ba9da7d1-3480-4c06-90f3-e7bff8c6f360" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCurrentAssetsReceivables_a455cddb-662a-46bb-b0de-6912a0f4ac9c" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCurrentAssetsReceivables"/>
    <link:calculationArc order="4" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedAssets_91a0aec9-d953-4c79-97b5-dcc481b8d95b" xlink:to="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCurrentAssetsReceivables_a455cddb-662a-46bb-b0de-6912a0f4ac9c" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCashAndEquivalents_83205f37-568a-4d2c-87b1-a7933afa356f" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCashAndEquivalents"/>
    <link:calculationArc order="5" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedAssets_91a0aec9-d953-4c79-97b5-dcc481b8d95b" xlink:to="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCashAndEquivalents_83205f37-568a-4d2c-87b1-a7933afa356f" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedNet_d543b721-0191-404e-8d9f-4ba63d441859" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedNet"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedLiabilities_0ebeaa13-3863-451a-ad55-3746bce7980c" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedLiabilities"/>
    <link:calculationArc order="1" weight="-1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedNet_d543b721-0191-404e-8d9f-4ba63d441859" xlink:to="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedLiabilities_0ebeaa13-3863-451a-ad55-3746bce7980c" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedAssets_3cd262bd-f683-4c97-a900-d943c9d77812" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedAssets"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedNet_d543b721-0191-404e-8d9f-4ba63d441859" xlink:to="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedAssets_3cd262bd-f683-4c97-a900-d943c9d77812" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredGoodwillAndLiabilitiesAssumedNet_b82ebaeb-ad02-49e6-93d0-66402db096b0" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredGoodwillAndLiabilitiesAssumedNet"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedNet_435ef508-cadc-4163-b6e1-da73c6675013" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedNet"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredGoodwillAndLiabilitiesAssumedNet_b82ebaeb-ad02-49e6-93d0-66402db096b0" xlink:to="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedNet_435ef508-cadc-4163-b6e1-da73c6675013" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_Goodwill_06187ac0-b04a-47df-862a-6ddf7c59bdb5" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_Goodwill"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredGoodwillAndLiabilitiesAssumedNet_b82ebaeb-ad02-49e6-93d0-66402db096b0" xlink:to="loc_us-gaap_Goodwill_06187ac0-b04a-47df-862a-6ddf7c59bdb5" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedLiabilities_b1cfb588-4684-42d7-aa68-7980160dc079" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedLiabilities"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCurrentLiabilitiesAccountsPayable_86b8f77b-f86e-40ad-bd7c-4d4a34a5a8c4" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCurrentLiabilitiesAccountsPayable"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedLiabilities_b1cfb588-4684-42d7-aa68-7980160dc079" xlink:to="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedCurrentLiabilitiesAccountsPayable_86b8f77b-f86e-40ad-bd7c-4d4a34a5a8c4" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedDeferredTaxLiabilities_b040c1ea-4c27-4146-a5ba-fb6802d46154" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedDeferredTaxLiabilities"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedLiabilities_b1cfb588-4684-42d7-aa68-7980160dc079" xlink:to="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedDeferredTaxLiabilities_b040c1ea-4c27-4146-a5ba-fb6802d46154" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://www.cantaloupe.com/role/ACQUISITIONSummaryofTotalConsiderationPaidforAcquisitionDetails" xlink:type="simple" xlink:href="ctlp-20230331.xsd#ACQUISITIONSummaryofTotalConsiderationPaidforAcquisitionDetails"/>
  <link:calculationLink xlink:role="http://www.cantaloupe.com/role/ACQUISITIONSummaryofTotalConsiderationPaidforAcquisitionDetails" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationConsiderationTransferred1_55b7e684-a160-48c1-9dd1-4122cca48b8a" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_BusinessCombinationConsiderationTransferred1"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsToAcquireBusinessesNetOfCashAcquired_c73881e0-bd47-42e7-80b8-934463996277" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PaymentsToAcquireBusinessesNetOfCashAcquired"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_BusinessCombinationConsiderationTransferred1_55b7e684-a160-48c1-9dd1-4122cca48b8a" xlink:to="loc_us-gaap_PaymentsToAcquireBusinessesNetOfCashAcquired_c73881e0-bd47-42e7-80b8-934463996277" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationConsiderationTransferredLiabilitiesIncurred_c5cfdeaa-9ba6-4400-acae-fa73073a4025" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_BusinessCombinationConsiderationTransferredLiabilitiesIncurred"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_BusinessCombinationConsiderationTransferred1_55b7e684-a160-48c1-9dd1-4122cca48b8a" xlink:to="loc_us-gaap_BusinessCombinationConsiderationTransferredLiabilitiesIncurred_c5cfdeaa-9ba6-4400-acae-fa73073a4025" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedNet_25738c7f-49b5-4b97-8cff-c9ccb1c9adcd" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedNet"/>
    <link:loc xlink:type="locator" xlink:label="loc_ctlp_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedTangibleAssets_def3f793-bab1-486f-958a-f6a87284d859" xlink:href="ctlp-20230331.xsd#ctlp_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedTangibleAssets"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedNet_25738c7f-49b5-4b97-8cff-c9ccb1c9adcd" xlink:to="loc_ctlp_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedTangibleAssets_def3f793-bab1-486f-958a-f6a87284d859" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedIntangibleAssetsOtherThanGoodwill_fb1e72ab-6a51-4242-b1ea-5dbe2ec3e1e0" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedIntangibleAssetsOtherThanGoodwill"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedNet_25738c7f-49b5-4b97-8cff-c9ccb1c9adcd" xlink:to="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedIntangibleAssetsOtherThanGoodwill_fb1e72ab-6a51-4242-b1ea-5dbe2ec3e1e0" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://www.cantaloupe.com/role/FINANCERECEIVABLESInformationRegardingFinanceReceivablesDetails" xlink:type="simple" xlink:href="ctlp-20230331.xsd#FINANCERECEIVABLESInformationRegardingFinanceReceivablesDetails"/>
  <link:calculationLink xlink:role="http://www.cantaloupe.com/role/FINANCERECEIVABLESInformationRegardingFinanceReceivablesDetails" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NotesReceivableNet_4bba7d5d-7114-48b7-b8a9-f1ac6a02a418" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_NotesReceivableNet"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NotesAndLoansReceivableNetCurrent_2f231763-8a9b-4e6c-95be-8c61d5391a0f" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_NotesAndLoansReceivableNetCurrent"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NotesReceivableNet_4bba7d5d-7114-48b7-b8a9-f1ac6a02a418" xlink:to="loc_us-gaap_NotesAndLoansReceivableNetCurrent_2f231763-8a9b-4e6c-95be-8c61d5391a0f" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NotesAndLoansReceivableNetNoncurrent_de46378f-3fd7-480c-92a6-620e5b1edb04" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_NotesAndLoansReceivableNetNoncurrent"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NotesReceivableNet_4bba7d5d-7114-48b7-b8a9-f1ac6a02a418" xlink:to="loc_us-gaap_NotesAndLoansReceivableNetNoncurrent_de46378f-3fd7-480c-92a6-620e5b1edb04" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://www.cantaloupe.com/role/FINANCERECEIVABLESSchedulebyYearofOriginationDetails" xlink:type="simple" xlink:href="ctlp-20230331.xsd#FINANCERECEIVABLESSchedulebyYearofOriginationDetails"/>
  <link:calculationLink xlink:role="http://www.cantaloupe.com/role/FINANCERECEIVABLESSchedulebyYearofOriginationDetails" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NotesReceivableGross_fa4350b4-f893-4357-9509-ffe4b39c75b7" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_NotesReceivableGross"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FinancingReceivableOriginatedFourYearsBeforeLatestFiscalYear_4e371220-77ba-45f9-8d8d-4cbf24b0adce" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_FinancingReceivableOriginatedFourYearsBeforeLatestFiscalYear"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NotesReceivableGross_fa4350b4-f893-4357-9509-ffe4b39c75b7" xlink:to="loc_us-gaap_FinancingReceivableOriginatedFourYearsBeforeLatestFiscalYear_4e371220-77ba-45f9-8d8d-4cbf24b0adce" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FinancingReceivableOriginatedFiveOrMoreYearsBeforeLatestFiscalYear_090dad7d-1414-4a6a-8590-77058f9b7a80" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_FinancingReceivableOriginatedFiveOrMoreYearsBeforeLatestFiscalYear"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NotesReceivableGross_fa4350b4-f893-4357-9509-ffe4b39c75b7" xlink:to="loc_us-gaap_FinancingReceivableOriginatedFiveOrMoreYearsBeforeLatestFiscalYear_090dad7d-1414-4a6a-8590-77058f9b7a80" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_ctlp_FinancingReceivableOriginatedMoreThanFiveYearsBeforeCurrentFiscalYearNet_2b22f44d-0898-4b2a-b8ee-ef5bfe689c0a" xlink:href="ctlp-20230331.xsd#ctlp_FinancingReceivableOriginatedMoreThanFiveYearsBeforeCurrentFiscalYearNet"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NotesReceivableGross_fa4350b4-f893-4357-9509-ffe4b39c75b7" xlink:to="loc_ctlp_FinancingReceivableOriginatedMoreThanFiveYearsBeforeCurrentFiscalYearNet_2b22f44d-0898-4b2a-b8ee-ef5bfe689c0a" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FinancingReceivableOriginatedThreeYearsBeforeLatestFiscalYear_e2150b97-4ef3-4442-8f5a-bea80d2f9be3" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_FinancingReceivableOriginatedThreeYearsBeforeLatestFiscalYear"/>
    <link:calculationArc order="4" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NotesReceivableGross_fa4350b4-f893-4357-9509-ffe4b39c75b7" xlink:to="loc_us-gaap_FinancingReceivableOriginatedThreeYearsBeforeLatestFiscalYear_e2150b97-4ef3-4442-8f5a-bea80d2f9be3" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FinancingReceivableOriginatedTwoYearsBeforeLatestFiscalYear_14a1498f-53c7-4e58-8c48-c1534b4e148e" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_FinancingReceivableOriginatedTwoYearsBeforeLatestFiscalYear"/>
    <link:calculationArc order="5" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NotesReceivableGross_fa4350b4-f893-4357-9509-ffe4b39c75b7" xlink:to="loc_us-gaap_FinancingReceivableOriginatedTwoYearsBeforeLatestFiscalYear_14a1498f-53c7-4e58-8c48-c1534b4e148e" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FinancingReceivableOriginatedInCurrentFiscalYear_add3c221-892f-45cf-89f6-fc1794363b31" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_FinancingReceivableOriginatedInCurrentFiscalYear"/>
    <link:calculationArc order="6" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NotesReceivableGross_fa4350b4-f893-4357-9509-ffe4b39c75b7" xlink:to="loc_us-gaap_FinancingReceivableOriginatedInCurrentFiscalYear_add3c221-892f-45cf-89f6-fc1794363b31" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FinancingReceivableOriginatedInFiscalYearBeforeLatestFiscalYear_075db3c0-8e2d-4ca1-9a76-007f2728745e" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_FinancingReceivableOriginatedInFiscalYearBeforeLatestFiscalYear"/>
    <link:calculationArc order="7" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NotesReceivableGross_fa4350b4-f893-4357-9509-ffe4b39c75b7" xlink:to="loc_us-gaap_FinancingReceivableOriginatedInFiscalYearBeforeLatestFiscalYear_075db3c0-8e2d-4ca1-9a76-007f2728745e" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://www.cantaloupe.com/role/FINANCERECEIVABLESSummaryofFinanceReceivablesFiscalYearsDetails" xlink:type="simple" xlink:href="ctlp-20230331.xsd#FINANCERECEIVABLESSummaryofFinanceReceivablesFiscalYearsDetails"/>
  <link:calculationLink xlink:role="http://www.cantaloupe.com/role/FINANCERECEIVABLESSummaryofFinanceReceivablesFiscalYearsDetails" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NotesReceivableNet_13abdcda-16a7-4f3b-8c06-299a9f3579f8" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_NotesReceivableNet"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FinancingReceivableBeforeAllowanceForCreditLossAndFee_91de6004-ba98-40bd-a703-9df105be7867" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_FinancingReceivableBeforeAllowanceForCreditLossAndFee"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NotesReceivableNet_13abdcda-16a7-4f3b-8c06-299a9f3579f8" xlink:to="loc_us-gaap_FinancingReceivableBeforeAllowanceForCreditLossAndFee_91de6004-ba98-40bd-a703-9df105be7867" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FinancingReceivableUnamortizedLoanCommitmentOriginationFeeAndPremiumDiscount_7560c4cf-8769-4a46-a8f9-594e3acabd63" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_FinancingReceivableUnamortizedLoanCommitmentOriginationFeeAndPremiumDiscount"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NotesReceivableNet_13abdcda-16a7-4f3b-8c06-299a9f3579f8" xlink:to="loc_us-gaap_FinancingReceivableUnamortizedLoanCommitmentOriginationFeeAndPremiumDiscount_7560c4cf-8769-4a46-a8f9-594e3acabd63" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FinancingReceivableAllowanceForCreditLosses_fcf27a5f-48d4-4885-bb6f-cf71004bce20" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_FinancingReceivableAllowanceForCreditLosses"/>
    <link:calculationArc order="3" weight="-1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NotesReceivableNet_13abdcda-16a7-4f3b-8c06-299a9f3579f8" xlink:to="loc_us-gaap_FinancingReceivableAllowanceForCreditLosses_fcf27a5f-48d4-4885-bb6f-cf71004bce20" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FinancingReceivableBeforeAllowanceForCreditLossAndFee_2294c3d3-2c16-4960-b6d5-3c9531b9668a" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_FinancingReceivableBeforeAllowanceForCreditLossAndFee"/>
    <link:loc xlink:type="locator" xlink:label="loc_ctlp_NotesAndLoansReceivableInYearTwo_d1a0e884-b76b-410b-b7da-5aee89a6d7a5" xlink:href="ctlp-20230331.xsd#ctlp_NotesAndLoansReceivableInYearTwo"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_FinancingReceivableBeforeAllowanceForCreditLossAndFee_2294c3d3-2c16-4960-b6d5-3c9531b9668a" xlink:to="loc_ctlp_NotesAndLoansReceivableInYearTwo_d1a0e884-b76b-410b-b7da-5aee89a6d7a5" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_ctlp_NotesAndLoansReceivableRemainderOfYear_40b1ffc0-d2e0-437c-ab6d-3e64e9dfdc19" xlink:href="ctlp-20230331.xsd#ctlp_NotesAndLoansReceivableRemainderOfYear"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_FinancingReceivableBeforeAllowanceForCreditLossAndFee_2294c3d3-2c16-4960-b6d5-3c9531b9668a" xlink:to="loc_ctlp_NotesAndLoansReceivableRemainderOfYear_40b1ffc0-d2e0-437c-ab6d-3e64e9dfdc19" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_ctlp_NotesAndLoansReceivableInYearThree_3a3fca39-bb5e-4287-80d6-38ab7b9e1c30" xlink:href="ctlp-20230331.xsd#ctlp_NotesAndLoansReceivableInYearThree"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_FinancingReceivableBeforeAllowanceForCreditLossAndFee_2294c3d3-2c16-4960-b6d5-3c9531b9668a" xlink:to="loc_ctlp_NotesAndLoansReceivableInYearThree_3a3fca39-bb5e-4287-80d6-38ab7b9e1c30" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_ctlp_NotesAndLoansReceivableInYearOne_96ff6f6e-341a-4e27-b978-10e99eb8c8d0" xlink:href="ctlp-20230331.xsd#ctlp_NotesAndLoansReceivableInYearOne"/>
    <link:calculationArc order="4" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_FinancingReceivableBeforeAllowanceForCreditLossAndFee_2294c3d3-2c16-4960-b6d5-3c9531b9668a" xlink:to="loc_ctlp_NotesAndLoansReceivableInYearOne_96ff6f6e-341a-4e27-b978-10e99eb8c8d0" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_ctlp_NotesAndLoansReceivableDueThereafter_7e5ab713-5244-4c29-93aa-7d3138929166" xlink:href="ctlp-20230331.xsd#ctlp_NotesAndLoansReceivableDueThereafter"/>
    <link:calculationArc order="5" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_FinancingReceivableBeforeAllowanceForCreditLossAndFee_2294c3d3-2c16-4960-b6d5-3c9531b9668a" xlink:to="loc_ctlp_NotesAndLoansReceivableDueThereafter_7e5ab713-5244-4c29-93aa-7d3138929166" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_ctlp_NotesAndLoansReceivableInYearFour_b4e9c061-76fd-4ef9-b619-d6e6f2f8a227" xlink:href="ctlp-20230331.xsd#ctlp_NotesAndLoansReceivableInYearFour"/>
    <link:calculationArc order="6" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_FinancingReceivableBeforeAllowanceForCreditLossAndFee_2294c3d3-2c16-4960-b6d5-3c9531b9668a" xlink:to="loc_ctlp_NotesAndLoansReceivableInYearFour_b4e9c061-76fd-4ef9-b619-d6e6f2f8a227" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://www.cantaloupe.com/role/EARNINGSLOSSPERSHARECALCULATIONCalculationofLossPerShareDetails" xlink:type="simple" xlink:href="ctlp-20230331.xsd#EARNINGSLOSSPERSHARECALCULATIONCalculationofLossPerShareDetails"/>
  <link:calculationLink xlink:role="http://www.cantaloupe.com/role/EARNINGSLOSSPERSHARECALCULATIONCalculationofLossPerShareDetails" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding_026270f3-b303-4bfe-8478-2dabf3b13346" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_WeightedAverageNumberOfSharesOutstandingBasic_43cd12dc-0d86-4162-b863-b459a740f91b" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_WeightedAverageNumberOfSharesOutstandingBasic"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding_026270f3-b303-4bfe-8478-2dabf3b13346" xlink:to="loc_us-gaap_WeightedAverageNumberOfSharesOutstandingBasic_43cd12dc-0d86-4162-b863-b459a740f91b" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_WeightedAverageNumberDilutedSharesOutstandingAdjustment_c52e3df7-1792-473c-9cbb-75a3a463e230" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_WeightedAverageNumberDilutedSharesOutstandingAdjustment"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding_026270f3-b303-4bfe-8478-2dabf3b13346" xlink:to="loc_us-gaap_WeightedAverageNumberDilutedSharesOutstandingAdjustment_c52e3df7-1792-473c-9cbb-75a3a463e230" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://www.cantaloupe.com/role/GOODWILLANDINTANGIBLEASSETSSummaryofAmortizableIntangibleAssetDetails" xlink:type="simple" xlink:href="ctlp-20230331.xsd#GOODWILLANDINTANGIBLEASSETSSummaryofAmortizableIntangibleAssetDetails"/>
  <link:calculationLink xlink:role="http://www.cantaloupe.com/role/GOODWILLANDINTANGIBLEASSETSSummaryofAmortizableIntangibleAssetDetails" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_Goodwill_27b0ff43-cf5c-4f0f-a776-cfe45ecae99c" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_Goodwill"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GoodwillGross_b65f5b61-851a-411a-ab4d-5b126d6cd088" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_GoodwillGross"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_Goodwill_27b0ff43-cf5c-4f0f-a776-cfe45ecae99c" xlink:to="loc_us-gaap_GoodwillGross_b65f5b61-851a-411a-ab4d-5b126d6cd088" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetsNet_2491a255-a39f-4e14-b81e-e88f3de76070" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_FiniteLivedIntangibleAssetsNet"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetsGross_149b774e-1475-4b25-b5f5-f86408023128" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_FiniteLivedIntangibleAssetsGross"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_FiniteLivedIntangibleAssetsNet_2491a255-a39f-4e14-b81e-e88f3de76070" xlink:to="loc_us-gaap_FiniteLivedIntangibleAssetsGross_149b774e-1475-4b25-b5f5-f86408023128" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetsAccumulatedAmortization_bc301618-7c72-405f-96ef-2cbfe6268c26" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_FiniteLivedIntangibleAssetsAccumulatedAmortization"/>
    <link:calculationArc order="2" weight="-1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_FiniteLivedIntangibleAssetsNet_2491a255-a39f-4e14-b81e-e88f3de76070" xlink:to="loc_us-gaap_FiniteLivedIntangibleAssetsAccumulatedAmortization_bc301618-7c72-405f-96ef-2cbfe6268c26" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://www.cantaloupe.com/role/DEBTANDOTHERFINANCINGARRANGEMENTSDebtandOtherFinancingArrangementSummaryDetails" xlink:type="simple" xlink:href="ctlp-20230331.xsd#DEBTANDOTHERFINANCINGARRANGEMENTSDebtandOtherFinancingArrangementSummaryDetails"/>
  <link:calculationLink xlink:role="http://www.cantaloupe.com/role/DEBTANDOTHERFINANCINGARRANGEMENTSDebtandOtherFinancingArrangementSummaryDetails" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LongTermDebt_09ed7199-2831-4d18-9f9d-689252903644" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LongTermDebt"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LongTermDebtCurrent_afe80710-35c5-44eb-af30-3e6d7ee196f2" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LongTermDebtCurrent"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_LongTermDebt_09ed7199-2831-4d18-9f9d-689252903644" xlink:to="loc_us-gaap_LongTermDebtCurrent_afe80710-35c5-44eb-af30-3e6d7ee196f2" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LongTermDebtNoncurrent_90476c83-218e-45fb-ab8a-fe8d4c8f60f5" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LongTermDebtNoncurrent"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_LongTermDebt_09ed7199-2831-4d18-9f9d-689252903644" xlink:to="loc_us-gaap_LongTermDebtNoncurrent_90476c83-218e-45fb-ab8a-fe8d4c8f60f5" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://www.cantaloupe.com/role/DEBTANDOTHERFINANCINGARRANGEMENTSDebtandOtherFinancingArrangementSummaryDetails_1" xlink:type="simple" xlink:href="ctlp-20230331.xsd#DEBTANDOTHERFINANCINGARRANGEMENTSDebtandOtherFinancingArrangementSummaryDetails_1"/>
  <link:calculationLink xlink:role="http://www.cantaloupe.com/role/DEBTANDOTHERFINANCINGARRANGEMENTSDebtandOtherFinancingArrangementSummaryDetails_1" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LongTermDebt_498061e2-4991-431b-86e8-eaea79a3cfe8" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LongTermDebt"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentCarryingAmount_e5bb01c4-1b76-48ae-a406-f0ec67554b9e" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DebtInstrumentCarryingAmount"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_LongTermDebt_498061e2-4991-431b-86e8-eaea79a3cfe8" xlink:to="loc_us-gaap_DebtInstrumentCarryingAmount_e5bb01c4-1b76-48ae-a406-f0ec67554b9e" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentUnamortizedDiscountPremiumAndDebtIssuanceCostsNet_9bd4b509-4eb9-459d-a129-bb7903a49dec" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DebtInstrumentUnamortizedDiscountPremiumAndDebtIssuanceCostsNet"/>
    <link:calculationArc order="2" weight="-1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_LongTermDebt_498061e2-4991-431b-86e8-eaea79a3cfe8" xlink:to="loc_us-gaap_DebtInstrumentUnamortizedDiscountPremiumAndDebtIssuanceCostsNet_9bd4b509-4eb9-459d-a129-bb7903a49dec" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://www.cantaloupe.com/role/DEBTANDOTHERFINANCINGARRANGEMENTSInterestExpenseDetails" xlink:type="simple" xlink:href="ctlp-20230331.xsd#DEBTANDOTHERFINANCINGARRANGEMENTSInterestExpenseDetails"/>
  <link:calculationLink xlink:role="http://www.cantaloupe.com/role/DEBTANDOTHERFINANCINGARRANGEMENTSInterestExpenseDetails" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_ctlp_InterestExpenseReversalOfExpense_7f485684-7db0-4caa-9058-fa45733d820d" xlink:href="ctlp-20230331.xsd#ctlp_InterestExpenseReversalOfExpense"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InterestExpenseDebt_29a23550-a181-47d5-9f1b-15ab5360cf54" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_InterestExpenseDebt"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_ctlp_InterestExpenseReversalOfExpense_7f485684-7db0-4caa-9058-fa45733d820d" xlink:to="loc_us-gaap_InterestExpenseDebt_29a23550-a181-47d5-9f1b-15ab5360cf54" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_ctlp_InterestExpenseReversalOfExpenseOther_d6e82caa-2d68-44a0-bfbf-4c3c902dd123" xlink:href="ctlp-20230331.xsd#ctlp_InterestExpenseReversalOfExpenseOther"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_ctlp_InterestExpenseReversalOfExpense_7f485684-7db0-4caa-9058-fa45733d820d" xlink:to="loc_ctlp_InterestExpenseReversalOfExpenseOther_d6e82caa-2d68-44a0-bfbf-4c3c902dd123" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://www.cantaloupe.com/role/ACCRUEDEXPENSESDetails" xlink:type="simple" xlink:href="ctlp-20230331.xsd#ACCRUEDEXPENSESDetails"/>
  <link:calculationLink xlink:role="http://www.cantaloupe.com/role/ACCRUEDEXPENSESDetails" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AccruedLiabilitiesCurrentAndNoncurrent_52c8a238-13f9-4a27-a4d4-6518c9c3f91b" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AccruedLiabilitiesCurrentAndNoncurrent"/>
    <link:loc xlink:type="locator" xlink:label="loc_ctlp_BusinessCombinationConsiderationWithheldInEscrowLiabilityCurrent_f4296305-2463-4c7d-8dd4-5aeb667028de" xlink:href="ctlp-20230331.xsd#ctlp_BusinessCombinationConsiderationWithheldInEscrowLiabilityCurrent"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_AccruedLiabilitiesCurrentAndNoncurrent_52c8a238-13f9-4a27-a4d4-6518c9c3f91b" xlink:to="loc_ctlp_BusinessCombinationConsiderationWithheldInEscrowLiabilityCurrent_f4296305-2463-4c7d-8dd4-5aeb667028de" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationContingentConsiderationLiabilityCurrent_91e473c9-9145-4cd1-9ec7-31e59adee984" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_BusinessCombinationContingentConsiderationLiabilityCurrent"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_AccruedLiabilitiesCurrentAndNoncurrent_52c8a238-13f9-4a27-a4d4-6518c9c3f91b" xlink:to="loc_us-gaap_BusinessCombinationContingentConsiderationLiabilityCurrent_91e473c9-9145-4cd1-9ec7-31e59adee984" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AccruedProfessionalFeesCurrentAndNoncurrent_9e1f2249-c66d-4e6a-810c-625836a9e4fc" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AccruedProfessionalFeesCurrentAndNoncurrent"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_AccruedLiabilitiesCurrentAndNoncurrent_52c8a238-13f9-4a27-a4d4-6518c9c3f91b" xlink:to="loc_us-gaap_AccruedProfessionalFeesCurrentAndNoncurrent_9e1f2249-c66d-4e6a-810c-625836a9e4fc" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OperatingLeaseLiabilityCurrent_c7a3e71a-f5a9-47dd-9aeb-bd4ccfba716a" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_OperatingLeaseLiabilityCurrent"/>
    <link:calculationArc order="4" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_AccruedLiabilitiesCurrentAndNoncurrent_52c8a238-13f9-4a27-a4d4-6518c9c3f91b" xlink:to="loc_us-gaap_OperatingLeaseLiabilityCurrent_c7a3e71a-f5a9-47dd-9aeb-bd4ccfba716a" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_ctlp_AccruedCompensationAndSalesCommissionsCurrentAndNoncurrent_3e8427fd-b16b-4a15-a78f-e34587d193f8" xlink:href="ctlp-20230331.xsd#ctlp_AccruedCompensationAndSalesCommissionsCurrentAndNoncurrent"/>
    <link:calculationArc order="5" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_AccruedLiabilitiesCurrentAndNoncurrent_52c8a238-13f9-4a27-a4d4-6518c9c3f91b" xlink:to="loc_ctlp_AccruedCompensationAndSalesCommissionsCurrentAndNoncurrent_3e8427fd-b16b-4a15-a78f-e34587d193f8" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SalesAndExciseTaxPayableCurrentAndNoncurrent_d827d4f5-427f-4712-b67b-967b27257144" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_SalesAndExciseTaxPayableCurrentAndNoncurrent"/>
    <link:calculationArc order="6" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_AccruedLiabilitiesCurrentAndNoncurrent_52c8a238-13f9-4a27-a4d4-6518c9c3f91b" xlink:to="loc_us-gaap_SalesAndExciseTaxPayableCurrentAndNoncurrent_d827d4f5-427f-4712-b67b-967b27257144" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherAccruedLiabilitiesCurrentAndNoncurrent_5dc54cd1-d73a-45fc-991f-e5438dc881cb" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_OtherAccruedLiabilitiesCurrentAndNoncurrent"/>
    <link:calculationArc order="7" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_AccruedLiabilitiesCurrentAndNoncurrent_52c8a238-13f9-4a27-a4d4-6518c9c3f91b" xlink:to="loc_us-gaap_OtherAccruedLiabilitiesCurrentAndNoncurrent_5dc54cd1-d73a-45fc-991f-e5438dc881cb" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AccruedIncomeTaxesCurrent_e13f50b2-1293-4892-885e-55ace893668d" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AccruedIncomeTaxesCurrent"/>
    <link:calculationArc order="8" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_AccruedLiabilitiesCurrentAndNoncurrent_52c8a238-13f9-4a27-a4d4-6518c9c3f91b" xlink:to="loc_us-gaap_AccruedIncomeTaxesCurrent_e13f50b2-1293-4892-885e-55ace893668d" xlink:type="arc"/>
  </link:calculationLink>
</link:linkbase>
