| Greece Football League U19 | 2019/01/26 11:30 | Apollon Pontou FC U19 v Iraklis U19 | W | 2-3 |
| Greece Super League 2 U19 | 2019/01/20 08:00 | Volos Nps U19 v Iraklis U19 | W | 1-4 |
| Greece Football League U19 | 2019/01/19 13:00 | Volos Nps U19 v Iraklis U19 | W | 1-4 |
| Greece Football League U19 | 2018/12/23 09:33 | Iraklis U19 v Kerkyra U19 | W | 4-0 |
| Greece Football League U19 | 2018/12/16 08:00 | Iraklis U19 v Apollon Larissa U19 | W | 6-0 |
| Greece Football League U19 | 2018/11/24 10:30 | Iraklis U19 v Aiginiakos U19 | W | 4-0 |
| Greece Football League U19 | 2018/12/22 12:04 | Apollon Pontou FC U19 v AE Karaiskakis U19 | L | 1-0 |
| Greece Football League U19 | 2018/12/16 08:00 | Doxa Dramas U19 v AE Karaiskakis U19 | D | 0-0 |
| Greece Football League U19 | 2018/11/24 12:00 | Kerkyra U19 v AE Karaiskakis U19 | L | 2-0 |
| Greece Football League U19 | 2018/05/12 12:30 | Apollon Larissa U19 v AE Karaiskakis U19 | W | 1-3 |
| Greece Football League U19 | 2018/05/02 13:00 | Aris Thessaloniki U19 v AE Karaiskakis U19 | L | 3-2 |
| Greece Football League U19 | 2018/04/02 12:30 | Anagennisi Karditsas U19 v AE Karaiskakis U19 | L | 2-1 |
| Greece Football League U19 | 2018/01/29 13:00 | AE Karaiskakis U19 v Aris Thessaloniki U19 | L | 0-1 |
| Greece Football League U19 | 2018/01/05 11:00 | Panserraikos U19 v AE Karaiskakis U19 | L | 4-1 |