1. Round | 29/09/2019 | Doxa Dramas FC | - | AE Karaiskakis | 2:3 | ||||
10. Round | 22/12/2019 | PAS Giannina | - | AE Karaiskakis | 2:0 | ||||
11. Round | 05/01/2020 | AE Karaiskakis | - | AO Kerkyra | 3:0 | ||||
12. Round | 12/01/2020 | AE Karaiskakis | - | Doxa Dramas FC | 2:2 | ||||
13. Round | 19/01/2020 | Apollon Lárissa | - | AE Karaiskakis | 2:0 | ||||
16. Round | 09/02/2020 | AE Karaiskakis | - | Ergotelis | 3:0 | ||||
18. Round | 22/02/2020 | Apollon Pontou | - | AE Karaiskakis | 1:3 | ||||
19. Round | 01/03/2020 | AE Karaiskakis | - | Apollon Smyrnis | 1:2 |