Home History
| 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 |
| Greece Football League 2 | 2019/03/31 13:00 | Enosi Panaspropirgiakou Doxa v Kalamata | L | 5-0 |
| Greece Football League 2 | 2019/03/24 13:00 | Kalamata v AO Ypatou | W | 1-0 |
| Greece Football League 2 | 2019/03/17 13:00 | Amvrysseas Distomou v Kalamata | W | 0-1 |
Away History
| Europe Friendlies | 2019/09/01 15:32 | Giannina v Karaiskakis | L | 2-1 |
| Greece Super League 2 | 2019/05/05 12:00 | Karaiskakis v Trikala | L | 1-3 |
| Greece Super League 2 | 2019/04/22 12:00 | Ergotelis v Karaiskakis | D | 1-1 |
| Greece Super League 2 | 2019/04/17 13:00 | Karaiskakis v Kissamikos | D | 0-0 |
| Greece Super League 2 | 2019/04/14 13:00 | Apollon Pontou FC v Karaiskakis | L | 2-1 |
| Greece Super League 2 | 2019/04/07 13:00 | Karaiskakis v Doxa Drama | D | 0-0 |
| Greece Super League 2 | 2019/03/31 13:00 | AE Sparti v Karaiskakis | W | 0-4 |
| Greece Super League 2 | 2019/03/27 13:00 | Aittitos Spata v Karaiskakis | W | 0-3 |