| 1. Round | 23/09/2023 | Olympiakos Piraeus II | - | GS Ilioupolis | 0:0 | ||||
| 2. Round | 01/10/2023 | GS Kallithea | - | Olympiakos Piraeus II | 3:2 | ||||
| 4. Round | 20/10/2023 | Panathinaikos II | - | Olympiakos Piraeus II | 1:3 |  |
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| 5. Round | 28/10/2023 | Olympiakos Piraeus II | - | AO Tilikratis | 4:1 | ||||
| 6. Round | 04/11/2023 | AO Giouchtas | - | Olympiakos Piraeus II | 2:2 | ||||
| 10. Round | 03/12/2023 | Olympiakos Piraeus II | - | PAE Chania | 3:0 | ||||
| 11. Round | 09/12/2023 | Panachaiki GE | - | Olympiakos Piraeus II | 1:1 | ||||
| 12. Round | 16/12/2023 | GS Ilioupolis | - | Olympiakos Piraeus II | 0:1 | ||||
| 13. Round | 06/01/2024 | Olympiakos Piraeus II | - | GS Kallithea | 1:2 | ||||
| 15. Round | 22/01/2024 | Panathinaikos II | - | Olympiakos Piraeus II | 1:3 | ||||
| 17. Round | 03/02/2024 | Olympiakos Piraeus II | - | AO Giouchtas | 3:1 | ||||
| 18. Round | 11/02/2024 | Diagoras FC | - | Olympiakos Piraeus II | 0:2 | ||||
| 19. Round | 19/02/2024 | Olympiakos Piraeus II | - | AO Egaleo | 0:0 | ||||
| 20. Round | 24/02/2024 | PS Kalamata | - | Olympiakos Piraeus II | 1:0 | ||||
| 21. Round | 03/03/2024 | PAE Chania | - | Olympiakos Piraeus II | 2:0 | ||||
| 22. Round | 10/03/2024 | Olympiakos Piraeus II | - | Panachaiki GE | 2:2 |
Greece