| 1. Round | 24/09/2023 | Ionikos Nikea | - | PAE Chania | 0:3 | ||||
| 2. Round | 02/10/2023 | PAE Chania | - | AO Tilikratis | 3:0 |  |
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| 3. Round | 16/10/2023 | Diagoras FC | - | PAE Chania | 3:1 | ||||
| 5. Round | 28/10/2023 | PAE Chania | - | Panachaiki GE | 4:1 | ||||
| 6. Round | 06/11/2023 | GS Kallithea | - | PAE Chania | 0:1 | ||||
| 7. Round | 12/11/2023 | PAE Chania | - | Panathinaikos II | 2:0 | ||||
| 10. Round | 03/12/2023 | Olympiakos Piraeus II | - | PAE Chania | 3:0 | ||||
| 11. Round | 10/12/2023 | GS Ilioupolis | - | PAE Chania | 1:0 | ||||
| 12. Round | 19/12/2023 | PAE Chania | - | Ionikos Nikea | 1:1 | ||||
| 13. Round | 07/01/2024 | AO Tilikratis | - | PAE Chania | 0:3 | ||||
| 16. Round | 28/01/2024 | Panachaiki GE | - | PAE Chania | 2:1 | |
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| 18. Round | 11/02/2024 | Panathinaikos II | - | PAE Chania | 0:2 | ||||
| 19. Round | 18/02/2024 | PAE Chania | - | AO Giouchtas | 4:1 | ||||
| 20. Round | 25/02/2024 | AO Egaleo | - | PAE Chania | 0:0 | ||||
| 21. Round | 03/03/2024 | PAE Chania | - | Olympiakos Piraeus II | 2:0 |
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