Company: CTLPP
Filing Date: 2025-10-10
Form Type: DEF 14A
Source: 0001628280-25-044777
Chunk: 0

Company: CANTALOUPE, INC.
Filing Date: 2025-10-10
Form: DEF 14A
Chunk 0
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UNITED STATES
SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

<div align='center'>SCHEDULE 14A

Proxy Statement Pursuant to Section 14(a) of the
Securities Exchange Act of 1934</div>

| ☑ |     | Filed by the Registrant |     | ☐ |     | Filed by a party other than the Registrant |

| CHECK THE APPROPRIATE BOX: |     |                                                                                 |
| ☐                          |     | Preliminary Proxy Statement                                                     |
| ☐                          |     | Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) |
| ☑                          |     | Definitive Proxy Statement                                                      |
| ☐                          |     | Definitive Additional Materials                                                 |
| ☐                          |     | Soliciting Material under §240.14a-12                                           |

#### Cantaloupe, Inc.
<div align='center'>(Name of Registrant as Specified In Its Charter)
(Name of Person(s) Filing Proxy Statement, if other than the Registrant)</div>

| PAYMENT OF FILING FEE (CHECK ALL BOXES THAT APPLY): |     |                                                                                                     |
| ☑                                                   |     | No fee required                                                                                     |
| ☐                                                   |     | Fee paid previously with preliminary materials                                                      |
| ☐                                                   |     | Fee computed on table in exhibit required by Item 25(b) per Exchange Act Rules 14a-6(i)(1) and 0-11 |

| Vision                                                             
 To be the global technology leader powering self-service commerce. |

#### A Message from our CEO and
Non-Executive Chair

| October 10, 2025                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                          
 Dear Shareholders,                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                        
 You are cordially invited to attend the 2026 Annual Meeting of Shareholders (the “Annual Meeting”) of Cantaloupe, Inc. (“Cantaloupe” or the “Company”) to be held online in a virtual format at 11:00 a.m., ET, on Wednesday, November 19, 2025, via live webcast atwww.virtualshareholdermeeting.com/CTLP2026.                                                                                                                                                                                                                                                                                                                                                                                                                           
 On behalf of the board and all of our employees, we thank you for your support of the Company and for your continued investment in Cantaloupe.                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                            
 Fiscal year 2025