| 1. Round | 30/08/2008 | Olympiakos Piraeus | - | Asteras Tripolis | 3:1 |  |
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| 2. Round | 13/09/2008 | Skoda Xanthi | - | Olympiakos Piraeus | 0:1 | ||||
| 3. Round | 21/09/2008 | Olympiakos Piraeus | - | Panserraikos | 4:1 | |
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| 4. Round | 27/09/2008 | OFI Heraklion | - | Olympiakos Piraeus | 0:0 | ||||
| 5. Round | 05/10/2008 | Olympiakos Piraeus | - | AEK Athen | 2:0 | |
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| 6. Round | 19/10/2008 | Olympiakos Piraeus | - | Panthrakikos | 2:0 | ||||
| 7. Round | 26/10/2008 | Aris Saloniki | - | Olympiakos Piraeus | 1:0 | ||||
| 8. Round | 02/11/2008 | Olympiakos Piraeus | - | Ergotelis | 2:0 | |
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| 9. Round | 09/11/2008 | Panathinaikos | - | Olympiakos Piraeus | 0:0 | ||||
| 10. Round | 16/11/2008 | Olympiakos Piraeus | - | PAOK Saloniki | 2:0 | ||||
| 11. Round | 22/11/2008 | Iraklis Saloniki | - | Olympiakos Piraeus | 0:3 | ||||
| 13. Round | 07/12/2008 | Olympiakos Piraeus | - | Levadiakos | 1:0 | ||||
| 14. Round | 13/12/2008 | AE Lárissa | - | Olympiakos Piraeus | 1:1 | ||||
| 15. Round | 21/12/2008 | Olympiakos Piraeus | - | Thrasyvoulos Fylis | 2:1 |
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