| 12. Round | 30/11/2008 | Panthrakikos | - | OFI Heraklion | 2:0 | ||||
| 14. Round | 14/12/2008 | Levadiakos | - | Panthrakikos | 2:0 | ||||
| 15. Round | 21/12/2008 | Panthrakikos | - | Aris Saloniki | 0:0 | ||||
| 21. Round | 07/02/2009 | Panthrakikos | - | Olympiakos Piraeus | 0:2 |  |
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| 28. Round | 05/04/2009 | Panthrakikos | - | AEK Athen | 1:1 | ||||
| 29. Round | 12/04/2009 | Panthrakikos | - | Levadiakos | 1:3 | ||||
| 30. Round | 26/04/2009 | Aris Saloniki | - | Panthrakikos | 3:2 |  |
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Greece