| 8. Round | 02/11/2008 | OFI Heraklion | - | Skoda Xanthi | 0:2 | ||||
| 9. Round | 08/11/2008 | Panserraikos | - | OFI Heraklion | 1:2 | ||||
| 11. Round | 23/11/2008 | OFI Heraklion | - | AEK Athen | 1:1 | ||||
| 12. Round | 30/11/2008 | Panthrakikos | - | OFI Heraklion | 2:0 |  |
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| 14. Round | 14/12/2008 | Ergotelis | - | OFI Heraklion | 1:3 | ||||
| 15. Round | 21/12/2008 | OFI Heraklion | - | Panathinaikos | 0:3 | ||||
| 16. Round | 04/01/2009 | PAOK Saloniki | - | OFI Heraklion | 2:0 | ||||
| 19. Round | 24/01/2009 | Olympiakos Piraeus | - | OFI Heraklion | 2:1 | |
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| 26. Round | 14/03/2009 | AEK Athen | - | OFI Heraklion | 1:0 | |
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| 28. Round | 05/04/2009 | Aris Saloniki | - | OFI Heraklion | 4:1 | ||||
| 29. Round | 12/04/2009 | OFI Heraklion | - | Ergotelis | 0:0 | ||||
| 30. Round | 26/04/2009 | Panathinaikos | - | OFI Heraklion | 3:1 |
Greece