| 1. Round | 24/08/2019 | Olympiakos Piraeus | - | Asteras Tripolis | 1:0 | ||||
| 3. Round | 15/09/2019 | Xanthi FC | - | Asteras Tripolis | 2:1 |  |
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| 4. Round | 21/09/2019 | Asteras Tripolis | - | Atromitos | 2:1 | ||||
| 5. Round | 29/09/2019 | OFI Heraklion | - | Asteras Tripolis | 3:1 | ||||
| 13. Round | 08/12/2019 | Asteras Tripolis | - | AE Lárissa | 1:1 | ||||
| 14. Round | 15/12/2019 | Asteras Tripolis | - | Olympiakos Piraeus | 0:5 |  |
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| 19. Round | 19/01/2020 | PAOK Saloniki | - | Asteras Tripolis | 3:1 | ||||
| 20. Round | 23/01/2020 | Asteras Tripolis | - | Panionios GSS | 2:0 | |
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| 21. Round | 27/01/2020 | Lamia | - | Asteras Tripolis | 1:1 | ||||
| 22. Round | 02/02/2020 | Asteras Tripolis | - | Panetolikos | 2:1 | ||||
| 23. Round | 09/02/2020 | Asteras Tripolis | - | Aris Saloniki | 1:1 | ||||
| 24. Round | 16/02/2020 | Volos NFC | - | Asteras Tripolis | 0:1 | ||||
| 25. Round | 22/02/2020 | Asteras Tripolis | - | Panathinaikos | 1:1 | ||||
| 26. Round | 01/03/2020 | AE Lárissa | - | Asteras Tripolis | 3:0 | |
Greece