| 1. Round | 29/09/2019 | Doxa Dramas FC | - | AE Karaiskakis | 2:3 | ||||
| 2. Round | 27/10/2019 | Apollon Pontou | - | Doxa Dramas FC | 0:1 | ||||
| 3. Round | 01/11/2019 | Doxa Dramas FC | - | Apollon Lárissa | 0:0 |  |
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| 4. Round | 10/11/2019 | Apollon Smyrnis | - | Doxa Dramas FC | 1:1 | ||||
| 5. Round | 15/11/2019 | Doxa Dramas FC | - | Panachaiki GE | 1:1 |  |
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| 8. Round | 08/12/2019 | PAS Giannina | - | Doxa Dramas FC | 1:0 | ||||
| 9. Round | 14/12/2019 | Doxa Dramas FC | - | Ergotelis | 1:2 | ||||
| 10. Round | 22/12/2019 | AO Kerkyra | - | Doxa Dramas FC | 0:2 |  |
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| 11. Round | 06/01/2020 | PAE Chania | - | Doxa Dramas FC | 2:1 | ||||
| 12. Round | 12/01/2020 | AE Karaiskakis | - | Doxa Dramas FC | 2:2 | ||||
| 14. Round | 26/01/2020 | Apollon Lárissa | - | Doxa Dramas FC | 4:1 | |
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| 15. Round | 03/02/2020 | Doxa Dramas FC | - | Apollon Smyrnis | 0:1 | ||||
| 16. Round | 10/02/2020 | Panachaiki GE | - | Doxa Dramas FC | 0:1 | ||||
| 17. Round | 16/02/2020 | Doxa Dramas FC | - | Platanias Chanion | 1:0 | ||||
| 18. Round | 21/02/2020 | Levadiakos | - | Doxa Dramas FC | 3:2 | |
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| 19. Round | 28/02/2020 | Doxa Dramas FC | - | PAS Giannina | 1:2 | |
Greece