Home History
| Greece Football League | 2019/11/03 13:00 | Iraklis 1908 FC v OF Ierapetras | L | 0-2 |
| Greece Football League | 2019/10/27 13:00 | Thesprotos v Iraklis 1908 FC | L | 3-0 |
| Greece Football League | 2019/10/20 13:00 | Iraklis 1908 FC v Trikala | L | 0-1 |
| Greece Football League | 2019/10/13 13:00 | Veria v Iraklis 1908 FC | L | 2-1 |
| Greece Football League | 2019/10/06 13:00 | Iraklis 1908 FC v Enosi Panaspropirgiakou Doxa | W | 2-0 |
| Greece Football League | 2019/09/29 13:00 | Kavala v Iraklis 1908 FC | L | 4-1 |
| Greece Cup | 2019/09/15 17:00 | Panserraikos v Iraklis 1908 FC | L | 2-0 |
| Greece Football League 2 | 2019/05/12 14:00 | Nestos Chrisoupolis v Iraklis 1908 FC | W | 0-1 |
Away History
| Greece Football League | 2019/11/03 13:00 | Kalamata v Olympiakos Volou | L | 1-2 |
| Greece Cup | 2019/10/30 13:00 | Kalamata v Larissa | W | 3-0 |
| Greece Football League | 2019/10/27 13:00 | Diagoras v Kalamata | L | 2-0 |
| Greece Football League | 2019/10/19 12:00 | Kalamata v Ionikos Nikea | W | 1-0 |
| Greece Football League | 2019/10/13 13:00 | Niki Volou v Kalamata | D | 1-1 |
| Greece Football League | 2019/10/06 12:00 | Kalamata v Ialysos | W | 2-0 |
| Greece Football League | 2019/09/29 12:00 | Egaleo v Kalamata | W | 0-2 |
| Greece Cup | 2019/09/25 15:00 | Kalamata v Karaiskakis | W | 4-3 |