| 6. Round | 19/10/2008 | Olympiakos Piraeus | - | Panthrakikos | 2:0 | ||||
| 9. Round | 09/11/2008 | Panathinaikos | - | Olympiakos Piraeus | 0:0 |  |
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| 18. Round | 17/01/2009 | Panserraikos | - | Olympiakos Piraeus | 0:1 | ||||
| 19. Round | 24/01/2009 | Olympiakos Piraeus | - | OFI Heraklion | 2:1 | ||||
| 28. Round | 05/04/2009 | Levadiakos | - | Olympiakos Piraeus | 1:2 | |
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| 29. Round | 12/04/2009 | Olympiakos Piraeus | - | AE Lárissa | 0:1 |
Greece