| 1. Round | 31/08/2008 | Aris Saloniki | - | Levadiakos | 2:0 | ||||
| 2. Round | 14/09/2008 | Levadiakos | - | Thrasyvoulos Fylis | 1:0 | ||||
| 3. Round | 21/09/2008 | Ergotelis | - | Levadiakos | 1:1 |  |
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| 4. Round | 28/09/2008 | Levadiakos | - | Asteras Tripolis | 1:0 | ||||
| 5. Round | 05/10/2008 | Panathinaikos | - | Levadiakos | 2:0 | ||||
| 6. Round | 19/10/2008 | Levadiakos | - | Skoda Xanthi | 0:0 | ||||
| 9. Round | 09/11/2008 | Iraklis Saloniki | - | Levadiakos | 1:0 | ||||
| 11. Round | 23/11/2008 | Panionios GSS | - | Levadiakos | 1:0 | ||||
| 12. Round | 30/11/2008 | Levadiakos | - | AEK Athen | 0:0 | |
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| 13. Round | 07/12/2008 | Olympiakos Piraeus | - | Levadiakos | 1:0 | |
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| 14. Round | 14/12/2008 | Levadiakos | - | Panthrakikos | 2:0 | ||||
| 15. Round | 21/12/2008 | AE Lárissa | - | Levadiakos | 2:1 | |
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| 21. Round | 08/02/2009 | Skoda Xanthi | - | Levadiakos | 4:0 |
Greece