| 4. Round | 17/09/2023 | AEK Athen | - | Olympiakos Piraeus | 1:1 | ||||
| 5. Round | 24/09/2023 | Olympiakos Piraeus | - | AE Kifisias | 4:0 |  |
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| 6. Round | 27/09/2023 | Olympiakos Piraeus | - | Aris Saloniki | 4:1 | |
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| 7. Round | 01/10/2023 | PAS Giannina | - | Olympiakos Piraeus | 0:3 | ||||
| 9. Round | 30/10/2023 | OFI Heraklion | - | Olympiakos Piraeus | 0:2 | ||||
| 10. Round | 05/11/2023 | Olympiakos Piraeus | - | PAOK Saloniki | 2:4 | ||||
| 11. Round | 12/11/2023 | Asteras Tripolis | - | Olympiakos Piraeus | 0:2 | ||||
| 12. Round | 25/11/2023 | Olympiakos Piraeus | - | Panetolikos | 3:1 | ||||
| 15. Round | 21/12/2023 | Atromitos | - | Olympiakos Piraeus | 0:0 | ||||
| 16. Round | 03/01/2024 | Lamia | - | Olympiakos Piraeus | 1:0 | ||||
| 20. Round | 28/01/2024 | Olympiakos Piraeus | - | PAS Giannina | 3:1 | |
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| 22. Round | 10/02/2024 | Olympiakos Piraeus | - | OFI Heraklion | 4:0 | ||||
| 24. Round | 25/02/2024 | Olympiakos Piraeus | - | Asteras Tripolis | 2:1 | ||||
| 25. Round | 28/02/2024 | Panetolikos | - | Olympiakos Piraeus | 1:2 | ||||
| 26. Round | 03/03/2024 | Olympiakos Piraeus | - | Volos NFC | 3:0 | |
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Montenegro
Serbia 
