| 1. Round | 30/08/2008 | Panthrakikos | - | Ergotelis | 1:2 | ||||
| 2. Round | 14/09/2008 | Ergotelis | - | Aris Saloniki | 3:0 | ||||
| 3. Round | 21/09/2008 | Ergotelis | - | Levadiakos | 1:1 | ||||
| 5. Round | 04/10/2008 | Ergotelis | - | PAOK Saloniki | 0:0 | ||||
| 6. Round | 18/10/2008 | Iraklis Saloniki | - | Ergotelis | 0:0 | ||||
| 7. Round | 26/10/2008 | Ergotelis | - | Panionios GSS | 2:5 | ||||
| 4. Round | 29/10/2008 | Panathinaikos | - | Ergotelis | 2:3 |  |
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| 8. Round | 02/11/2008 | Olympiakos Piraeus | - | Ergotelis | 2:0 | ||||
| 9. Round | 09/11/2008 | Ergotelis | - | AE Lárissa | 2:1 | ||||
| 10. Round | 16/11/2008 | Ergotelis | - | Thrasyvoulos Fylis | 1:2 | ||||
| 11. Round | 23/11/2008 | Asteras Tripolis | - | Ergotelis | 3:1 | ||||
| 12. Round | 30/11/2008 | Ergotelis | - | Skoda Xanthi | 0:0 | ||||
| 13. Round | 06/12/2008 | Panserraikos | - | Ergotelis | 0:2 | ||||
| 14. Round | 14/12/2008 | Ergotelis | - | OFI Heraklion | 1:3 | ||||
| 15. Round | 21/12/2008 | AEK Athen | - | Ergotelis | 3:2 | ||||
| 16. Round | 03/01/2009 | Ergotelis | - | Panthrakikos | 0:1 | ||||
| 17. Round | 11/01/2009 | Aris Saloniki | - | Ergotelis | 0:0 | |
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| 18. Round | 18/01/2009 | Levadiakos | - | Ergotelis | 4:0 |
Greece