| 1. Ronde | 25.08.2019 | AEK Athene | - | Xanthi FC | 1:2 |  |
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| 2. Ronde | 31.08.2019 | Panetolikos | - | Xanthi FC | 1:2 | ||||
| 17. Ronde | 05.01.2020 | Xanthi FC | - | AE Lárissa | 2:1 | ||||
| 18. Ronde | 11.01.2020 | Volos NFC | - | Xanthi FC | 1:3 |  |
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| 19. Ronde | 19.01.2020 | Xanthi FC | - | Panathinaikos | 0:1 | |
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| 20. Ronde | 23.01.2020 | Aris Saloniki | - | Xanthi FC | 1:0 | |
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| 21. Ronde | 26.01.2020 | Xanthi FC | - | OFI Heraklion | 2:2 | |
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| 24. Ronde | 16.02.2020 | Xanthi FC | - | Lamia | 0:0 | ||||
| 25. Ronde | 23.02.2020 | Atromitos | - | Xanthi FC | 1:0 | |
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| 26. Ronde | 01.03.2020 | Xanthi FC | - | PAOK Saloniki | 1:1 |
Griekenland