| 1. Round | 23/09/2023 | Olympiakos Piraeus II | - | GS Ilioupolis | 0:0 | ||||
| 3. Round | 14/10/2023 | Olympiakos Piraeus II | - | Ionikos Nikea | 1:1 | ||||
| 4. Round | 20/10/2023 | Panathinaikos II | - | Olympiakos Piraeus II | 1:3 | ||||
| 5. Round | 28/10/2023 | Olympiakos Piraeus II | - | AO Tilikratis | 4:1 | ||||
| 6. Round | 04/11/2023 | AO Giouchtas | - | Olympiakos Piraeus II | 2:2 | ||||
| 7. Round | 11/11/2023 | Olympiakos Piraeus II | - | Diagoras FC | 1:0 | ||||
| 8. Round | 18/11/2023 | AO Egaleo | - | Olympiakos Piraeus II | 0:0 | ||||
| 9. Round | 26/11/2023 | Olympiakos Piraeus II | - | PS Kalamata | 0:0 | ||||
| 11. Round | 09/12/2023 | Panachaiki GE | - | Olympiakos Piraeus II | 1:1 | ||||
| 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