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