Weather: Good Stadium: Agioi Anargyroi Municipal Stadium Pitch: Good Round: 23
Referee: Dimitris Maloutas Home Manager: Apostolos Charalampidis Away Manager: Jose Manuel Roca
| Greece Super League 2 | 2018/12/09 13:00 | Iraklis v Karaiskakis | W | 0-1 |
| Greece Super League 2 | 2019/01/19 13:00 | Kissamikos v Karaiskakis | L | 1-0 |
| Greece Super League 2 | 2019/01/13 13:00 | Karaiskakis v Apollon Pontou FC | L | 0-2 |
| Greece Super League 2 | 2018/12/23 13:00 | Karaiskakis v AE Sparti | D | 0-0 |
| Greece Super League 2 | 2018/12/16 13:00 | Karaiskakis v Aittitos Spata | W | 1-0 |
| Greece Super League 2 | 2018/12/09 13:00 | Iraklis v Karaiskakis | W | 0-1 |
| Greece Super League 2 | 2018/12/02 13:00 | Karaiskakis v Apollon Larissa | L | 0-1 |
| Greece Super League 2 | 2018/11/25 13:00 | Panachaiki v Karaiskakis | D | 0-0 |
| Greece Super League 2 | 2018/11/21 13:00 | Karaiskakis v Aiginiakos FC | W | 4-0 |
| Greece Super League 2 | 2019/01/20 13:00 | Trikala v Iraklis | D | 0-0 |
| Greece Super League 2 | 2019/01/13 13:00 | Iraklis v Ergotelis | W | 2-1 |
| Greece Super League 2 | 2019/01/05 13:00 | Kissamikos v Iraklis | W | 0-1 |
| Greece Super League 2 | 2018/12/23 13:00 | Iraklis v Apollon Pontou FC | L | 0-2 |
| Greece Cup | 2018/12/18 17:30 | Iraklis v Giannina | W | 2-0 |
| Greece Super League 2 | 2018/12/15 13:00 | Doxa Drama v Iraklis | L | 2-0 |
| Greece Super League 2 | 2018/12/09 13:00 | Iraklis v Karaiskakis | L | 0-1 |
| Greece Super League 2 | 2018/12/02 13:00 | Aittitos Spata v Iraklis | W | 0-3 |