| 22. Round | 14/02/2009 | Levadiakos | - | PAOK Saloniki | 0:3 | ||||
| 23. Round | 22/02/2009 | Panserraikos | - | Levadiakos | 1:0 | ||||
| 24. Round | 01/03/2009 | Levadiakos | - | Iraklis Saloniki | 3:0 |  |
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| 25. Round | 08/03/2009 | OFI Heraklion | - | Levadiakos | 0:2 | ||||
| 26. Round | 15/03/2009 | Levadiakos | - | Panionios GSS | 1:1 | |
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| 27. Round | 22/03/2009 | AEK Athen | - | Levadiakos | 3:1 | ||||
| 28. Round | 05/04/2009 | Levadiakos | - | Olympiakos Piraeus | 1:2 | ||||
| 29. Round | 12/04/2009 | Panthrakikos | - | Levadiakos | 1:3 | |
Italy