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| 1st(1st leg) | Panserraikos | - | Panathinaikos | 0:0 | ||
| 2nd (2nd leg) | Panathinaikos | - | Panserraikos | 2:3 | ||
| 1st(1st leg): 04/02/2009 17:00 | 2nd (2nd leg): 04/03/2009 17:00 | Winner: Panserraikos | ||||
| 1st(1st leg) | PAOK Saloniki | - | Olympiakos Piraeus | 1:0 | ||
| 2nd (2nd leg) | Olympiakos Piraeus | - | PAOK Saloniki | 2:0 aet | ||
| 1st(1st leg): 04/02/2009 19:15 | 2nd (2nd leg): 04/03/2009 19:15 | Winner: Olympiakos Piraeus | ||||
| 1st(1st leg) | Panionios GSS | - | Asteras Tripolis | 0:1 | ||
| 2nd (2nd leg) | Asteras Tripolis | - | Panionios GSS | 1:0 | ||
| 1st(1st leg): 18/02/2009 14:45 | 2nd (2nd leg): 04/03/2009 14:00 | Winner: Asteras Tripolis | ||||
| 1st(1st leg) | Skoda Xanthi | - | AEK Athen | 2:1 | ||
| 2nd (2nd leg) | AEK Athen | - | Skoda Xanthi | 1:0 | ||
| 1st(1st leg): 18/02/2009 19:30 | 2nd (2nd leg): 25/02/2009 17:00 | Winner: AEK Athen | ||||
