| 2023-12-03 13:00 | Grp.B | GS Ilioupolis |  | 2-0 |  | Egaleo | Michalis Bastakos 58', Pavlos Pantelidis 61' (pen.) | |
| 2023-10-22 12:00 | Grp.B | GS Ilioupolis | | 1-0 |  | Diagoras Rodos | Michalis Stamatoulas 90' (o.g.) | |
| 2023-10-01 14:00 | Grp.B | GS Ilioupolis | | 0-3 |  | Ionikos | Giannis Ikonomidis 21', Tomás de Vincenti 39', Abiola Dauda 90' | |
| 2023-09-13 14:00 | 3E | GS Ilioupolis | | 1-2(a.e.t.) |  | Levadiakos FC |
