1. Round | 24/08/2019 | Olympiakos Piraeus | - | Asteras Tripolis | 1:0 | ||||
3. Round | 14/09/2019 | Olympiakos Piraeus | - | Volos NFC | 5:0 | ||||
4. Round | 22/09/2019 | Panathinaikos | - | Olympiakos Piraeus | 1:1 | ||||
6. Round | 06/10/2019 | Aris Saloniki | - | Olympiakos Piraeus | 1:2 | ||||
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 | ||||
10. Round | 10/11/2019 | Olympiakos Piraeus | - | Atromitos | 2:0 | ||||
11. Round | 23/11/2019 | Panionios GSS | - | Olympiakos Piraeus | 1:1 | ||||
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 | ||||
16. Round | 22/12/2019 | Volos NFC | - | Olympiakos Piraeus | 0:0 | ||||
18. Round | 12/01/2020 | Lamia | - | Olympiakos Piraeus | 0:4 |