| 1. Round | 25/08/2019 | AEK Athen | - | Xanthi FC | 1:2 |  |
|||
| 2. Round | 31/08/2019 | Panetolikos | - | Xanthi FC | 1:2 | ||||
| 3. Round | 15/09/2019 | Xanthi FC | - | Asteras Tripolis | 2:1 | ||||
| 4. Round | 22/09/2019 | AE Lárissa | - | Xanthi FC | 3:0 |  |
|||
| 5. Round | 29/09/2019 | Xanthi FC | - | Volos NFC | 3:1 | ||||
| 8. Round | 26/10/2019 | OFI Heraklion | - | Xanthi FC | 2:0 | |
|||
| 11. Round | 23/11/2019 | Lamia | - | Xanthi FC | 1:0 | ||||
| 12. Round | 01/12/2019 | Xanthi FC | - | Atromitos | 1:0 | ||||
| 13. Round | 07/12/2019 | PAOK Saloniki | - | Xanthi FC | 2:0 | ||||
| 14. Round | 14/12/2019 | Xanthi FC | - | AEK Athen | 0:1 | |
|||
| 15. Round | 18/12/2019 | Xanthi FC | - | Panetolikos | 0:0 | ||||
| 16. Round | 21/12/2019 | Asteras Tripolis | - | Xanthi FC | 5:0 | ||||
| 17. Round | 05/01/2020 | Xanthi FC | - | AE Lárissa | 2:1 | ||||
| 19. Round | 19/01/2020 | Xanthi FC | - | Panathinaikos | 0:1 |  |
|||
| 21. Round | 26/01/2020 | Xanthi FC | - | OFI Heraklion | 2:2 | ||||
| 22. Round | 01/02/2020 | Olympiakos Piraeus | - | Xanthi FC | 3:1 | |
|||
| 23. Round | 08/02/2020 | Panionios GSS | - | Xanthi FC | 0:0 | ||||
| 25. Round | 23/02/2020 | Atromitos | - | Xanthi FC | 1:0 | ||||
| 26. Round | 01/03/2020 | Xanthi FC | - | PAOK Saloniki | 1:1 |
Uruguay