1. Round | 30/08/2008 | OFI Heraklion | - | PAOK Saloniki | 0:2 | ||||
2. Round | 13/09/2008 | Iraklis Saloniki | - | OFI Heraklion | 1:1 | ||||
3. Round | 21/09/2008 | Panionios GSS | - | OFI Heraklion | 1:1 | ||||
4. Round | 27/09/2008 | OFI Heraklion | - | Olympiakos Piraeus | 0:0 | ||||
5. Round | 04/10/2008 | AE Lárissa | - | OFI Heraklion | 4:3 | ||||
6. Round | 19/10/2008 | OFI Heraklion | - | Thrasyvoulos Fylis | 1:3 | ||||
7. Round | 25/10/2008 | Asteras Tripolis | - | OFI Heraklion | 2:2 | ||||
8. Round | 02/11/2008 | OFI Heraklion | - | Skoda Xanthi | 0:2 | ||||
9. Round | 08/11/2008 | Panserraikos | - | OFI Heraklion | 1:2 | ||||
10. Round | 16/11/2008 | Levadiakos | - | OFI Heraklion | 2:1 | ||||
11. Round | 23/11/2008 | OFI Heraklion | - | AEK Athen | 1:1 | ||||
13. Round | 06/12/2008 | OFI Heraklion | - | Aris Saloniki | 0:1 | ||||
14. Round | 14/12/2008 | Ergotelis | - | OFI Heraklion | 1:3 | ||||
16. Round | 04/01/2009 | PAOK Saloniki | - | OFI Heraklion | 2:0 | ||||
17. Round | 11/01/2009 | OFI Heraklion | - | Iraklis Saloniki | 2:3 |