| 1. Round | 24/08/2019 | Olympiakos Piraeus | - | Asteras Tripolis | 1:0 | ||||
| 2. Round | 01/09/2019 | AE Lárissa | - | Olympiakos Piraeus | 0:1 | ||||
| 3. Round | 14/09/2019 | Olympiakos Piraeus | - | Volos NFC | 5:0 | ||||
| 4. Round | 22/09/2019 | Panathinaikos | - | Olympiakos Piraeus | 1:1 | ||||
| 13. Round | 07/12/2019 | Panetolikos | - | Olympiakos Piraeus | 0:3 | ||||
| 14. Round | 15/12/2019 | Asteras Tripolis | - | Olympiakos Piraeus | 0:5 | ||||
| 24. Round | 15/02/2020 | Olympiakos Piraeus | - | Panionios GSS | 4:0 | ||||
| 25. Round | 23/02/2020 | PAOK Saloniki | - | Olympiakos Piraeus | 0:1 | ||||
| 26. Round | 01/03/2020 | Olympiakos Piraeus | - | Panetolikos | 2:0 |
Serbia