| 1. Round | 16/01/2021 | AE Karaiskakis | - | Levadiakos | 0:2 | ||||
| 2. Round | 20/01/2021 | OFI Ierapetra | - | AE Karaiskakis | 2:2 | ||||
| 3. Round | 24/01/2021 | AE Karaiskakis | - | PAE Chania | 1:1 | ||||
| 4. Round | 27/01/2021 | Panachaiki GE | - | AE Karaiskakis | 2:2 | ||||
| 6. Round | 07/02/2021 | Apollon Lárissa | - | AE Karaiskakis | 3:0 | ||||
| 7. Round | 10/02/2021 | AE Karaiskakis | - | Xanthi FC | 0:1 | ||||
| 8. Round | 14/02/2021 | Ionikos Nikea | - | AE Karaiskakis | 2:0 | ||||
| 9. Round | 17/02/2021 | AE Karaiskakis | - | AO Trikala | 1:0 |  |
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| 10. Round | 20/02/2021 | Doxa Dramas FC | - | AE Karaiskakis | 0:0 | ||||
| 11. Round | 27/02/2021 | Diagoras FC | - | AE Karaiskakis | 1:0 | |
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| 12. Round | 03/03/2021 | Levadiakos | - | AE Karaiskakis | 4:0 | ||||
| 15. Round | 17/03/2021 | AE Karaiskakis | - | Panachaiki GE | 0:0 | ||||
| 16. Round | 20/03/2021 | Ergotelis | - | AE Karaiskakis | 0:1 | ||||
| 17. Round | 28/03/2021 | AE Karaiskakis | - | Apollon Lárissa | 1:2 | ||||
| 19. Round | 07/04/2021 | AE Karaiskakis | - | Ionikos Nikea | 0:3 | ||||
| 20. Round | 11/04/2021 | AO Trikala | - | AE Karaiskakis | 1:0 | ||||
| 21. Round | 18/04/2021 | AE Karaiskakis | - | Doxa Dramas FC | 1:1 |
Germany