| 2. Round | 30/08/2009 | AE Lárissa | - | Olympiakos Piraeus | 0:2 | ||||
| 3. Round | 12/09/2009 | Olympiakos Piraeus | - | AO Kavala | 0:0 | ||||
| 4. Round | 20/09/2009 | PAOK Saloniki | - | Olympiakos Piraeus | 1:2 | ||||
| 1. Round | 23/09/2009 | AEK Athen | - | Olympiakos Piraeus | 1:2 |  |
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| 5. Round | 26/09/2009 | Olympiakos Piraeus | - | Panionios GSS | 1:0 | |
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| 6. Round | 03/10/2009 | Levadiakos | - | Olympiakos Piraeus | 0:3 |  |
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| 7. Round | 17/10/2009 | Olympiakos Piraeus | - | Asteras Tripolis | 3:0 | |
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| 8. Round | 24/10/2009 | Olympiakos Piraeus | - | Ergotelis | 2:1 | |
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| 10. Round | 07/11/2009 | Olympiakos Piraeus | - | Iraklis Saloniki | 1:1 | ||||
| 11. Round | 21/11/2009 | PAS Giannina | - | Olympiakos Piraeus | 2:2 | ||||
| 12. Round | 29/11/2009 | Olympiakos Piraeus | - | Panathinaikos | 2:0 | |
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| 13. Round | 05/12/2009 | Skoda Xanthi | - | Olympiakos Piraeus | 0:1 | ||||
| 14. Round | 13/12/2009 | Olympiakos Piraeus | - | Panthrakikos | 3:0 | |
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| 15. Round | 20/12/2009 | Aris Saloniki | - | Olympiakos Piraeus | 1:0 | ||||
| 19. Round | 24/01/2010 | Olympiakos Piraeus | - | PAOK Saloniki | 0:1 | ||||
| 20. Round | 31/01/2010 | Panionios GSS | - | Olympiakos Piraeus | 0:1 |
Brazil