| 5. Round | 28/09/2019 | Olympiakos Piraeus | - | Lamia | 2:0 | ||||
| 13. Round | 07/12/2019 | Panetolikos | - | Olympiakos Piraeus | 0:3 | ||||
| 15. Round | 18/12/2019 | Olympiakos Piraeus | - | AE Lárissa | 4:1 | ||||
| 16. Round | 22/12/2019 | Volos NFC | - | Olympiakos Piraeus | 0:0 | ||||
| 17. Round | 05/01/2020 | Olympiakos Piraeus | - | Panathinaikos | 1:0 | ||||
| 18. Round | 12/01/2020 | Lamia | - | Olympiakos Piraeus | 0:4 |  |
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| 19. Round | 19/01/2020 | Olympiakos Piraeus | - | Aris Saloniki | 4:2 | ||||
| 20. Round | 22/01/2020 | OFI Heraklion | - | Olympiakos Piraeus | 0:1 | ||||
| 21. Round | 26/01/2020 | AEK Athen | - | Olympiakos Piraeus | 0:0 | ||||
| 22. Round | 01/02/2020 | Olympiakos Piraeus | - | Xanthi FC | 3:1 | ||||
| 23. Round | 09/02/2020 | Atromitos | - | Olympiakos Piraeus | 0:1 | ||||
| 24. Round | 15/02/2020 | Olympiakos Piraeus | - | Panionios GSS | 4:0 | ||||
| 25. Round | 23/02/2020 | PAOK Saloniki | - | Olympiakos Piraeus | 0:1 | |
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| 26. Round | 01/03/2020 | Olympiakos Piraeus | - | Panetolikos | 2:0 | |
Senegal