| 1. Ronde | 29.09.2019 | Doxa Dramas FC | - | AE Karaiskakis | 2:3 |  |
 |
||
| 2. Ronde | 27.10.2019 | Apollon Pontou | - | Doxa Dramas FC | 0:1 | |
|||
| 3. Ronde | 01.11.2019 | Doxa Dramas FC | - | Apollon Lárissa | 0:0 | ||||
| 4. Ronde | 10.11.2019 | Apollon Smyrnis | - | Doxa Dramas FC | 1:1 | ||||
| 5. Ronde | 15.11.2019 | Doxa Dramas FC | - | Panachaiki GE | 1:1 | ||||
| 6. Ronde | 22.11.2019 | Platanias Chanion | - | Doxa Dramas FC | 1:3 | |
|
||
| 7. Ronde | 01.12.2019 | Doxa Dramas FC | - | Levadiakos | 0:0 | ||||
| 8. Ronde | 08.12.2019 | PAS Giannina | - | Doxa Dramas FC | 1:0 | |
|||
| 9. Ronde | 14.12.2019 | Doxa Dramas FC | - | Ergotelis | 1:2 | |
Duitsland
