| 1. Round | 20/08/2023 | Olympiakos Piraeus | - | Panserraikos | 2:0 |  |
|||
| 2. Round | 27/08/2023 | Olympiakos Piraeus | - | Atromitos | 4:0 | ||||
| 3. Round | 03/09/2023 | Olympiakos Piraeus | - | Lamia | 4:0 |  |
|||
| 4. Round | 17/09/2023 | AEK Athen | - | Olympiakos Piraeus | 1:1 | |
|||
| 5. Round | 24/09/2023 | Olympiakos Piraeus | - | AE Kifisias | 4:0 | ||||
| 6. Round | 27/09/2023 | Olympiakos Piraeus | - | Aris Saloniki | 4:1 | ||||
| 7. Round | 01/10/2023 | PAS Giannina | - | Olympiakos Piraeus | 0:3 | ||||
| 9. Round | 30/10/2023 | OFI Heraklion | - | Olympiakos Piraeus | 0:2 | ||||
| 11. Round | 12/11/2023 | Asteras Tripolis | - | Olympiakos Piraeus | 0:2 | ||||
| 12. Round | 25/11/2023 | Olympiakos Piraeus | - | Panetolikos | 3:1 | ||||
| 13. Round | 03/12/2023 | Volos NFC | - | Olympiakos Piraeus | 2:2 | ||||
| 14. Round | 18/12/2023 | Panserraikos | - | Olympiakos Piraeus | 0:1 | ||||
| 16. Round | 03/01/2024 | Lamia | - | Olympiakos Piraeus | 1:0 |
Spain