| 1. Round | 30/08/2008 | Olympiakos Piraeus | - | Asteras Tripolis | 3:1 | ||||
| 2. Round | 14/09/2008 | Asteras Tripolis | - | AE Lárissa | 0:0 | ||||
| 3. Round | 21/09/2008 | Thrasyvoulos Fylis | - | Asteras Tripolis | 0:2 | ||||
| 4. Round | 28/09/2008 | Levadiakos | - | Asteras Tripolis | 1:0 | ||||
| 5. Round | 05/10/2008 | Asteras Tripolis | - | Skoda Xanthi | 0:0 | ||||
| 6. Round | 18/10/2008 | Panserraikos | - | Asteras Tripolis | 0:0 | ||||
| 7. Round | 25/10/2008 | Asteras Tripolis | - | OFI Heraklion | 2:2 | ||||
| 8. Round | 02/11/2008 | AEK Athen | - | Asteras Tripolis | 2:1 |
Portugal