| 5. Round | 28/09/2019 | Olympiakos Piraeus | - | Lamia | 2:0 | ||||
| 6. Round | 06/10/2019 | Aris Saloniki | - | Olympiakos Piraeus | 1:2 |  |
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| 7. Round | 19/10/2019 | Olympiakos Piraeus | - | OFI Heraklion | 2:1 | ||||
| 8. Round | 27/10/2019 | Olympiakos Piraeus | - | AEK Athen | 2:0 | ||||
| 9. Round | 02/11/2019 | Xanthi FC | - | Olympiakos Piraeus | 0:0 | |
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| 10. Round | 10/11/2019 | Olympiakos Piraeus | - | Atromitos | 2:0 |  |
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| 12. Round | 01/12/2019 | Olympiakos Piraeus | - | PAOK Saloniki | 1:1 | ||||
| 14. Round | 15/12/2019 | Asteras Tripolis | - | Olympiakos Piraeus | 0:5 | ||||
| 15. Round | 18/12/2019 | Olympiakos Piraeus | - | AE Lárissa | 4:1 | ||||
| 24. Round | 15/02/2020 | Olympiakos Piraeus | - | Panionios GSS | 4:0 |
Australia
