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| 1st(1st leg) | Omonia Nikosia | - | APOP Kinyras | 0:0 | ||
| 2nd (2nd leg) | APOP Kinyras | - | Omonia Nikosia | 3:0 | ||
| 1st(1st leg): 25/02/2009 14:00 | 2nd (2nd leg): 11/03/2009 14:00 | Winner: APOP Kinyras | ||||
| 1st(1st leg) | Ethnikos Achna | - | AEL Limassol | 1:1 | ||
| 2nd (2nd leg) | AEL Limassol | - | Ethnikos Achna | 2:0 | ||
| 1st(1st leg): 25/02/2009 16:00 | 2nd (2nd leg): 11/03/2009 16:00 | Winner: AEL Limassol | ||||
| 1st(1st leg) | Ermis Aradippou | - | APOEL Nikosia | 1:1 | ||
| 2nd (2nd leg) | APOEL Nikosia | - | Ermis Aradippou | 3:0 | ||
| 1st(1st leg): 04/03/2009 14:00 | 2nd (2nd leg): 18/03/2009 14:00 | Winner: APOEL Nikosia | ||||
| 1st(1st leg) | Apollon Limassol | - | Enosis Neon Paralimni | 2:1 | ||
| 2nd (2nd leg) | Enosis Neon Paralimni | - | Apollon Limassol | 3:2 | ||
| 1st(1st leg): 04/03/2009 16:00 | 2nd (2nd leg): 18/03/2009 16:00 | Winner: Apollon Limassol | ||||
