Home History
| 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 |
| Greece Cup | 2019/09/25 13:00 | Kalamata v Karaiskakis | D | 0-0 |
| Europe Friendlies | 2019/09/05 14:30 | Koropi v Kalamata | W | 0-2 |
| Greece Football League 2 | 2019/05/15 12:00 | Kalamata v Diagoras | W | 2-1 |
| Greece Football League 2 | 2019/05/08 13:00 | Diagoras v Kalamata | L | 1-0 |
| Greece Football League 2 | 2019/04/14 13:00 | Kalamata v Panarkadikos | D | 2-2 |
| Greece Football League 2 | 2019/04/07 13:00 | AE Ermionidas v Kalamata | W | 0-2 |
Away History
| 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 |
| Greece Football League 2 | 2019/05/05 14:00 | Iraklis 1908 FC v Nestos Chrisoupolis | D | 0-0 |
| Greece Football League 2 | 2019/04/14 14:00 | Makedonikos v Iraklis 1908 FC | W | 0-2 |
| Greece Football League 2 | 2019/04/07 13:00 | Iraklis 1908 FC v Anagennisi Giannitsa | W | 3-1 |
| Greece Football League 2 | 2019/03/31 13:00 | Agrotikos Asteras v Iraklis 1908 FC | W | 0-3 |
| Greece Football League 2 | 2019/03/24 13:00 | Iraklis 1908 FC v Olympiakos Kyminon | W | 3-0 |
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