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| U | Ermis Aradippou | - | ENTHOI Lakatamia | 3:1 | ||
| R | ENTHOI Lakatamia | - | Ermis Aradippou | 1:4 | ||
| U: 14.01.2009 14:00 | R: 28.01.2009 14:00 | Winnaars: Ermis Aradippou | ||||
| U | Omonia Nikosia | - | Dighenis Morphou | 3:1 | ||
| R | Dighenis Morphou | - | Omonia Nikosia | 1:2 | ||
| U: 14.01.2009 15:00 | R: 28.01.2009 15:00 | Winnaars: Omonia Nikosia | ||||
| U | AEK Larnaca | - | APOP Kinyras | 0:2 | ||
| R | APOP Kinyras | - | AEK Larnaca | 1:1 | ||
| U: 14.01.2009 15:00 | R: 28.01.2009 16:00 | Winnaars: APOP Kinyras | ||||
| U | AE Paphos | - | AEL Limassol | 0:1 | ||
| R | AEL Limassol | - | AE Paphos | 2:1 | ||
| U: 14.01.2009 17:00 | R: 28.01.2009 17:00 | Winnaars: AEL Limassol | ||||
| U | Ethnikos Assias | - | Ethnikos Achna | 1:5 | ||
| R | Ethnikos Achna | - | Ethnikos Assias | 3:1 | ||
| U: 21.01.2009 14:00 | R: 04.02.2009 14:00 | Winnaars: Ethnikos Achna | ||||
| U | APOEL Nicosia | - | Doxa Katokopias | 2:2 | ||
| R | Doxa Katokopias | - | APOEL Nicosia | 2:3 | ||
| U: 21.01.2009 15:00 | R: 04.02.2009 15:00 | Winnaars: APOEL Nicosia | ||||
| U | Atromitos Yeroskipou | - | Enosis Neon Paralimni | 0:0 | ||
| R | Enosis Neon Paralimni | - | Atromitos Yeroskipou | 3:0 | ||
| U: 21.01.2009 16:00 | R: 04.02.2009 14:00 | Winnaars: Enosis Neon Paralimni | ||||
| U | Anorthosis Famagusta | - | Apollon Limassol | 2:1 | ||
| R | Apollon Limassol | - | Anorthosis Famagusta | 3:1 n.v. | ||
| U: 21.01.2009 17:00 | R: 04.02.2009 17:00 | Winnaars: Apollon Limassol | ||||
