1. Round | 29/09/2019 | Doxa Dramas FC | - | AE Karaiskakis | 2:3 | ||||
2. Round | 26/10/2019 | AE Karaiskakis | - | Apollon Lárissa | 2:0 | ||||
3. Round | 03/11/2019 | Panachaiki GE | - | AE Karaiskakis | 2:0 | ||||
4. Round | 10/11/2019 | AE Karaiskakis | - | Levadiakos | 1:1 | ||||
5. Round | 17/11/2019 | Ergotelis | - | AE Karaiskakis | 4:2 | ||||
11. Round | 05/01/2020 | AE Karaiskakis | - | AO Kerkyra | 3:0 | ||||
12. Round | 12/01/2020 | AE Karaiskakis | - | Doxa Dramas FC | 2:2 | ||||
18. Round | 22/02/2020 | Apollon Pontou | - | AE Karaiskakis | 1:3 | ||||
20. Round | 06/03/2020 | Platanias Chanion | - | AE Karaiskakis | 1:0 |