| 2. Round | 18/09/2020 | Olympiakos Piraeus | - | Asteras Tripolis | 3:0 | ||||
| 4. Round | 04/10/2020 | PAS Giannina | - | Olympiakos Piraeus | 1:1 |  |
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| 5. Round | 17/10/2020 | Olympiakos Piraeus | - | Atromitos | 4:0 | |
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| 11. Round | 05/12/2020 | Olympiakos Piraeus | - | Volos NFC | 4:1 | |
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| 13. Round | 20/12/2020 | Olympiakos Piraeus | - | AE Lárissa | 5:1 | ||||
| 14. Round | 03/01/2021 | Olympiakos Piraeus | - | AEK Athen | 3:0 | |
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| 15. Round | 06/01/2021 | Asteras Tripolis | - | Olympiakos Piraeus | 0:4 | |
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| 16. Round | 09/01/2021 | Panetolikos | - | Olympiakos Piraeus | 1:2 | ||||
| 6. Round | 13/01/2021 | PAOK Saloniki | - | Olympiakos Piraeus | 1:1 |  |
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| 18. Round | 24/01/2021 | Atromitos | - | Olympiakos Piraeus | 0:1 | |
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| 19. Round | 27/01/2021 | Olympiakos Piraeus | - | PAOK Saloniki | 3:0 | ||||
| 20. Round | 31/01/2021 | Apollon Smyrnis | - | Olympiakos Piraeus | 1:3 | ||||
| 21. Round | 07/02/2021 | Olympiakos Piraeus | - | OFI Heraklion | 3:0 | ||||
| 22. Round | 14/02/2021 | Panathinaikos | - | Olympiakos Piraeus | 2:1 |  |
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| 24. Round | 01/03/2021 | Volos NFC | - | Olympiakos Piraeus | 1:2 | ||||
| 25. Round | 07/03/2021 | Olympiakos Piraeus | - | Lamia | 3:0 |
Senegal