| 16. Round | 03/01/2024 | Lamia | - | Olympiakos Piraeus | 1:0 |  |
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| 17. Round | 07/01/2024 | Olympiakos Piraeus | - | AEK Athen | 1:2 | ||||
| 18. Round | 14/01/2024 | AE Kifisias | - | Olympiakos Piraeus | 2:3 |  |
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| 19. Round | 21/01/2024 | Aris Saloniki | - | Olympiakos Piraeus | 1:2 | |
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| 20. Round | 28/01/2024 | Olympiakos Piraeus | - | PAS Giannina | 3:1 | |
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| 21. Round | 04/02/2024 | Panathinaikos | - | Olympiakos Piraeus | 2:0 | ||||
| 22. Round | 10/02/2024 | Olympiakos Piraeus | - | OFI Heraklion | 4:0 | ||||
| 23. Round | 18/02/2024 | PAOK Saloniki | - | Olympiakos Piraeus | 1:4 | |
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| 24. Round | 25/02/2024 | Olympiakos Piraeus | - | Asteras Tripolis | 2:1 | ||||
| 26. Round | 03/03/2024 | Olympiakos Piraeus | - | Volos NFC | 3:0 |
Spain