| 1. Round | 30/08/2008 | Olympiakos Piraeus | - | Asteras Tripolis | 3:1 |  |
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| 9. Round | 09/11/2008 | Asteras Tripolis | - | Panthrakikos | 0:0 | ||||
| 11. Round | 23/11/2008 | Asteras Tripolis | - | Ergotelis | 3:1 | |
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| 19. Round | 25/01/2009 | Asteras Tripolis | - | Levadiakos | 2:0 | ||||
| 24. Round | 01/03/2009 | Panthrakikos | - | Asteras Tripolis | 0:0 | ||||
| 26. Round | 15/03/2009 | Ergotelis | - | Asteras Tripolis | 0:1 | ||||
| 27. Round | 22/03/2009 | Asteras Tripolis | - | Panathinaikos | 1:1 | ||||
| 30. Round | 26/04/2009 | Asteras Tripolis | - | Panionios GSS | 3:4 |
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Italy