| 1. Round | 24/08/2019 | Olympiakos Piraeus | - | Asteras Tripolis | 1:0 | ||||
| 2. Round | 01/09/2019 | Asteras Tripolis | - | AEK Athen | 2:3 | ||||
| 3. Round | 15/09/2019 | Xanthi FC | - | Asteras Tripolis | 2:1 | ||||
| 4. Round | 21/09/2019 | Asteras Tripolis | - | Atromitos | 2:1 |  |
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| 5. Round | 29/09/2019 | OFI Heraklion | - | Asteras Tripolis | 3:1 | ||||
| 6. Round | 06/10/2019 | Asteras Tripolis | - | PAOK Saloniki | 1:2 | ||||
| 7. Round | 20/10/2019 | Panionios GSS | - | Asteras Tripolis | 0:1 | |
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| 8. Round | 28/10/2019 | Asteras Tripolis | - | Lamia | 4:1 | |
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| 9. Round | 03/11/2019 | Panetolikos | - | Asteras Tripolis | 1:1 | ||||
| 10. Round | 10/11/2019 | Aris Saloniki | - | Asteras Tripolis | 2:1 | ||||
| 11. Round | 24/11/2019 | Asteras Tripolis | - | Volos NFC | 0:0 | |
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| 12. Round | 01/12/2019 | Panathinaikos | - | Asteras Tripolis | 1:0 | |
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| 13. Round | 08/12/2019 | Asteras Tripolis | - | AE Lárissa | 1:1 | ||||
| 14. Round | 15/12/2019 | Asteras Tripolis | - | Olympiakos Piraeus | 0:5 | ||||
| 16. Round | 21/12/2019 | Asteras Tripolis | - | Xanthi FC | 5:0 |  |
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| 17. Round | 04/01/2020 | Atromitos | - | Asteras Tripolis | 2:1 |
Spain