| 1. Round | 20/08/2023 | Olympiakos Piraeus | - | Panserraikos | 2:0 | ||||
| 2. Round | 27/08/2023 | Olympiakos Piraeus | - | Atromitos | 4:0 |  |
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| 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 |  |
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| 9. Round | 30/10/2023 | OFI Heraklion | - | Olympiakos Piraeus | 0:2 | ||||
| 10. Round | 05/11/2023 | Olympiakos Piraeus | - | PAOK Saloniki | 2:4 | ||||
| 12. Round | 25/11/2023 | Olympiakos Piraeus | - | Panetolikos | 3:1 | ||||
| 18. Round | 14/01/2024 | AE Kifisias | - | Olympiakos Piraeus | 2:3 | ||||
| 19. Round | 21/01/2024 | Aris Saloniki | - | Olympiakos Piraeus | 1:2 | ||||
| 20. Round | 28/01/2024 | Olympiakos Piraeus | - | PAS Giannina | 3:1 | ||||
| 21. Round | 04/02/2024 | Panathinaikos | - | Olympiakos Piraeus | 2:0 | |
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| 25. Round | 28/02/2024 | Panetolikos | - | Olympiakos Piraeus | 1:2 | |
Spain