| 13. Round | 19/01/2019 | Chania Kissamikos | - | AE Karaiskakis | 1:0 | ||||
| 14. Round | 27/01/2019 | AE Karaiskakis | - | Ergotelis | 1:0 | ||||
| 11. Round | 30/01/2019 | Doxa Dramas FC | - | AE Karaiskakis | 2:0 | ||||
| 15. Round | 03/02/2019 | AO Trikala | - | AE Karaiskakis | 0:0 | ||||
| 16. Round | 10/02/2019 | AE Karaiskakis | - | Volos NFC | 0:1 | ||||
| 17. Round | 17/02/2019 | Platanias Chanion | - | AE Karaiskakis | 2:0 | ||||
| 18. Round | 24/02/2019 | AE Karaiskakis | - | Irodotos | 1:0 | ||||
| 20. Round | 06/03/2019 | Aiginiakos FC | - | AE Karaiskakis | 1:2 | ||||
| 21. Round | 09/03/2019 | AE Karaiskakis | - | Panachaiki GE | 0:1 | ||||
| 22. Round | 17/03/2019 | Apollon Lárissa | - | AE Karaiskakis | 0:1 |  |
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| 23. Round | 24/03/2019 | AE Karaiskakis | - | AEP Iraklis FC | 1:0 | ||||
| 25. Round | 31/03/2019 | Sparta FC | - | AE Karaiskakis | 0:4 | ||||
| 27. Round | 14/04/2019 | Apollon Pontou | - | AE Karaiskakis | 2:1 | ||||
| 28. Round | 17/04/2019 | AE Karaiskakis | - | Chania Kissamikos | 0:0 | ||||
| 29. Round | 22/04/2019 | Ergotelis | - | AE Karaiskakis | 1:1 |  |
Spain