| 1. Round | 28/08/2005 | Panathinaikos | - | Olympiakos Piraeus | 0:2 |  |
|||
| 2. Round | 10/09/2005 | Olympiakos Piraeus | - | Panionios GSS | 5:0 | ||||
| 3. Round | 17/09/2005 | GS Kallithea | - | Olympiakos Piraeus | 0:3 | ||||
| 4. Round | 24/09/2005 | Olympiakos Piraeus | - | Akratitos Liosion | 2:0 | ||||
| 8. Round | 29/10/2005 | Apollon Kalamarias | - | Olympiakos Piraeus | 1:2 | ||||
| 9. Round | 06/11/2005 | Olympiakos Piraeus | - | Skoda Xanthi | 2:0 | ||||
| 11. Round | 28/11/2005 | Olympiakos Piraeus | - | Iraklis Saloniki | 2:1 | |
|||
| 13. Round | 12/12/2005 | Olympiakos Piraeus | - | AE Lárissa | 4:0 | ||||
| 15. Round | 08/01/2006 | Ionikos Nikea | - | Olympiakos Piraeus | 0:1 | ||||
| 17. Round | 30/01/2006 | Panionios GSS | - | Olympiakos Piraeus | 2:3 | ||||
| 18. Round | 06/02/2006 | Olympiakos Piraeus | - | GS Kallithea | 2:1 | ||||
| 19. Round | 13/02/2006 | Akratitos Liosion | - | Olympiakos Piraeus | 0:1 | ||||
| 29. Round | 30/04/2006 | Levadiakos | - | Olympiakos Piraeus | 3:2 | ||||
| 30. Round | 14/05/2006 | Olympiakos Piraeus | - | Ionikos Nikea | 0:0 |
Greece