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| 1st(1st leg) | Ermis Aradippou | - | ENTHOI Lakatamia | 3:1 | ||
| 2nd (2nd leg) | ENTHOI Lakatamia | - | Ermis Aradippou | 1:4 | ||
| 1st(1st leg): 14/01/2009 13:00 | 2nd (2nd leg): 28/01/2009 13:00 | Winner: Ermis Aradippou | ||||
| 1st(1st leg) | Omonia Nikosia | - | Dighenis Morphou | 3:1 | ||
| 2nd (2nd leg) | Dighenis Morphou | - | Omonia Nikosia | 1:2 | ||
| 1st(1st leg): 14/01/2009 14:00 | 2nd (2nd leg): 28/01/2009 14:00 | Winner: Omonia Nikosia | ||||
| 1st(1st leg) | AEK Larnaca | - | APOP Kinyras | 0:2 | ||
| 2nd (2nd leg) | APOP Kinyras | - | AEK Larnaca | 1:1 | ||
| 1st(1st leg): 14/01/2009 14:00 | 2nd (2nd leg): 28/01/2009 15:00 | Winner: APOP Kinyras | ||||
| 1st(1st leg) | AE Paphos | - | AEL Limassol | 0:1 | ||
| 2nd (2nd leg) | AEL Limassol | - | AE Paphos | 2:1 | ||
| 1st(1st leg): 14/01/2009 16:00 | 2nd (2nd leg): 28/01/2009 16:00 | Winner: AEL Limassol | ||||
| 1st(1st leg) | Ethnikos Assias | - | Ethnikos Achna | 1:5 | ||
| 2nd (2nd leg) | Ethnikos Achna | - | Ethnikos Assias | 3:1 | ||
| 1st(1st leg): 21/01/2009 13:00 | 2nd (2nd leg): 04/02/2009 13:00 | Winner: Ethnikos Achna | ||||
| 1st(1st leg) | APOEL Nikosia | - | Doxa Katokopias | 2:2 | ||
| 2nd (2nd leg) | Doxa Katokopias | - | APOEL Nikosia | 2:3 | ||
| 1st(1st leg): 21/01/2009 14:00 | 2nd (2nd leg): 04/02/2009 14:00 | Winner: APOEL Nikosia | ||||
| 1st(1st leg) | Atromitos Yeroskipou | - | Enosis Neon Paralimni | 0:0 | ||
| 2nd (2nd leg) | Enosis Neon Paralimni | - | Atromitos Yeroskipou | 3:0 | ||
| 1st(1st leg): 21/01/2009 15:00 | 2nd (2nd leg): 04/02/2009 13:00 | Winner: Enosis Neon Paralimni | ||||
| 1st(1st leg) | Anorthosis Famagusta | - | Apollon Limassol | 2:1 | ||
| 2nd (2nd leg) | Apollon Limassol | - | Anorthosis Famagusta | 3:1 aet | ||
| 1st(1st leg): 21/01/2009 16:00 | 2nd (2nd leg): 04/02/2009 16:00 | Winner: Apollon Limassol | ||||
