| 3. Round | 11/10/2023 | Anagennisi Karditsa | - | Aiolikos Mytilinis | 3:1 | ||||
| 4. Round | 15/10/2023 | Makedonikos FC | - | Anagennisi Karditsa | 0:0 | ||||
| 6. Round | 29/10/2023 | Anagennisi Karditsa | - | AE Lárissa | 0:2 | ||||
| 7. Round | 04/11/2023 | PAOK Saloniki II | - | Anagennisi Karditsa | 2:0 |  |
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| 10. Round | 19/11/2023 | Anagennisi Karditsa | - | Levadiakos | 2:0 | ||||
| 11. Round | 26/11/2023 | Anagennisi Karditsa | - | Niki Volou FC | 2:0 | ||||
| 12. Round | 03/12/2023 | Apollon Pontou | - | Anagennisi Karditsa | 2:1 | ||||
| 14. Round | 17/12/2023 | AEK Athen II | - | Anagennisi Karditsa | 0:0 | ||||
| 15. Round | 03/01/2024 | Anagennisi Karditsa | - | AEP Iraklis FC | 2:1 | ||||
| 16. Round | 07/01/2024 | Aiolikos Mytilinis | - | Anagennisi Karditsa | 1:1 | ||||
| 17. Round | 14/01/2024 | Anagennisi Karditsa | - | Makedonikos FC | 0:1 | ||||
| 18. Round | 21/01/2024 | Anagennisi Karditsa | - | Kozani FC | 1:1 | ||||
| 19. Round | 28/01/2024 | AE Lárissa | - | Anagennisi Karditsa | 1:0 | ||||
| 20. Round | 03/02/2024 | Anagennisi Karditsa | - | PAOK Saloniki II | 0:3 |
Croatia