| 1. Round | 25/08/2019 | AEK Athen | - | Xanthi FC | 1:2 | ||||
| 2. Round | 31/08/2019 | Panetolikos | - | Xanthi FC | 1:2 | ||||
| 4. Round | 22/09/2019 | AE Lárissa | - | Xanthi FC | 3:0 | ||||
| 5. Round | 29/09/2019 | Xanthi FC | - | Volos NFC | 3:1 | ||||
| 6. Round | 05/10/2019 | Panathinaikos | - | Xanthi FC | 0:1 | ||||
| 7. Round | 20/10/2019 | Xanthi FC | - | Aris Saloniki | 0:1 | ||||
| 8. Round | 26/10/2019 | OFI Heraklion | - | Xanthi FC | 2:0 | ||||
| 10. Round | 10/11/2019 | Xanthi FC | - | Panionios GSS | 1:2 | ||||
| 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 | ||||
| 15. Round | 18/12/2019 | Xanthi FC | - | Panetolikos | 0:0 |
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