| 1. Round | 23/09/2023 | Olympiakos Piraeus II | - | GS Ilioupolis | 0:0 | ||||
| 2. Round | 01/10/2023 | GS Kallithea | - | Olympiakos Piraeus II | 3:2 |  |
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| 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 |  |
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| 7. Round | 11/11/2023 | Olympiakos Piraeus II | - | Diagoras FC | 1:0 | ||||
| 9. Round | 26/11/2023 | Olympiakos Piraeus II | - | PS Kalamata | 0:0 | ||||
| 15. Round | 22/01/2024 | Panathinaikos II | - | Olympiakos Piraeus II | 1:3 |
Cyprus