| Ethniki B | 13/01/19 | AE Karaiskakis | - | Apollon Pontou | 0:2 | ||||
| Ethniki B | 14/04/19 | Apollon Pontou | - | AE Karaiskakis | 2:1 | ||||
| SL2 | 24/11/19 | AE Karaiskakis | - | PAE Chania | 0:0 | ||||
| SL2 | 16/02/20 | PAE Chania | - | AE Karaiskakis | 5:1 | ||||
| SL2 | 24/01/21 | AE Karaiskakis | - | PAE Chania | 1:1 | ||||
| SL2 | 13/03/21 | PAE Chania | - | AE Karaiskakis | 1:0 | ||||
| Kypello | 26/09/21 | AE Karaiskakis | - | Xanthi FC | 0:2 | ||||
| SL2 | 13/04/22 | AE Karaiskakis | - | AO Egaleo | 3:1 |  |
Greece