| 1. Round | 30/08/2008 | Olympiakos Piraeus | - | Asteras Tripolis | 3:1 | ||||
| 3. Round | 21/09/2008 | Olympiakos Piraeus | - | Panserraikos | 4:1 | ||||
| 5. Round | 05/10/2008 | Olympiakos Piraeus | - | AEK Athen | 2:0 |  |
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| 7. Round | 26/10/2008 | Aris Saloniki | - | Olympiakos Piraeus | 1:0 | ||||
| 9. Round | 09/11/2008 | Panathinaikos | - | Olympiakos Piraeus | 0:0 | ||||
| 10. Round | 16/11/2008 | Olympiakos Piraeus | - | PAOK Saloniki | 2:0 | |
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| 11. Round | 22/11/2008 | Iraklis Saloniki | - | Olympiakos Piraeus | 0:3 | ||||
| 14. Round | 13/12/2008 | AE Lárissa | - | Olympiakos Piraeus | 1:1 | |
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| 16. Round | 03/01/2009 | Asteras Tripolis | - | Olympiakos Piraeus | 0:1 | |
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| 17. Round | 10/01/2009 | Olympiakos Piraeus | - | Skoda Xanthi | 2:1 | ||||
| 20. Round | 01/02/2009 | AEK Athen | - | Olympiakos Piraeus | 0:1 | ||||
| 21. Round | 07/02/2009 | Panthrakikos | - | Olympiakos Piraeus | 0:2 | ||||
| 22. Round | 14/02/2009 | Olympiakos Piraeus | - | Aris Saloniki | 2:1 | |
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| 23. Round | 22/02/2009 | Ergotelis | - | Olympiakos Piraeus | 1:0 | ||||
| 27. Round | 22/03/2009 | Panionios GSS | - | Olympiakos Piraeus | 2:3 | ||||
| 30. Round | 26/04/2009 | Thrasyvoulos Fylis | - | Olympiakos Piraeus | 0:2 |
France