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 | ||||
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 | ||||
9. Round | 02/11/2019 | Xanthi FC | - | Olympiakos Piraeus | 0:0 |