| 1. Round | 29/09/2019 | Apollon Smyrnis | - | Ergotelis | 3:0 | ||||
| 2. Round | 27/10/2019 | PAE Chania | - | Apollon Smyrnis | 0:1 | ||||
| 3. Round | 03/11/2019 | Apollon Smyrnis | - | Apollon Pontou | 4:0 | ||||
| 4. Round | 10/11/2019 | Apollon Smyrnis | - | Doxa Dramas FC | 1:1 | ||||
| 5. Round | 17/11/2019 | Platanias Chanion | - | Apollon Smyrnis | 0:1 | ||||
| 16. Round | 09/02/2020 | Apollon Smyrnis | - | Platanias Chanion | 4:0 | ||||
| 18. Round | 23/02/2020 | Apollon Smyrnis | - | AO Kerkyra | 2:1 |  |
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| 19. Round | 01/03/2020 | AE Karaiskakis | - | Apollon Smyrnis | 1:2 | ||||
| 20. Round | 09/03/2020 | Apollon Smyrnis | - | Apollon Lárissa | 3:0 |
Greece