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| H (Match allé) | Ermis Aradippou | - | ENTHOI Lakatamia | 3:1 | ||
| R (match retour) | ENTHOI Lakatamia | - | Ermis Aradippou | 1:4 | ||
| H (Match allé): 14.01.2009 14:00 | R (match retour): 28.01.2009 14:00 | vainqueur: Ermis Aradippou | ||||
| H (Match allé) | Omonia Nikosia | - | Dighenis Morphou | 3:1 | ||
| R (match retour) | Dighenis Morphou | - | Omonia Nikosia | 1:2 | ||
| H (Match allé): 14.01.2009 15:00 | R (match retour): 28.01.2009 15:00 | vainqueur: Omonia Nikosia | ||||
| H (Match allé) | AEK Larnaca | - | APOP Kinyras | 0:2 | ||
| R (match retour) | APOP Kinyras | - | AEK Larnaca | 1:1 | ||
| H (Match allé): 14.01.2009 15:00 | R (match retour): 28.01.2009 16:00 | vainqueur: APOP Kinyras | ||||
| H (Match allé) | AE Paphos | - | AEL Limassol | 0:1 | ||
| R (match retour) | AEL Limassol | - | AE Paphos | 2:1 | ||
| H (Match allé): 14.01.2009 17:00 | R (match retour): 28.01.2009 17:00 | vainqueur: AEL Limassol | ||||
| H (Match allé) | Ethnikos Assias | - | Ethnikos Achna | 1:5 | ||
| R (match retour) | Ethnikos Achna | - | Ethnikos Assias | 3:1 | ||
| H (Match allé): 21.01.2009 14:00 | R (match retour): 04.02.2009 14:00 | vainqueur: Ethnikos Achna | ||||
| H (Match allé) | APOEL Nikosia | - | Doxa Katokopias | 2:2 | ||
| R (match retour) | Doxa Katokopias | - | APOEL Nikosia | 2:3 | ||
| H (Match allé): 21.01.2009 15:00 | R (match retour): 04.02.2009 15:00 | vainqueur: APOEL Nikosia | ||||
| H (Match allé) | Atromitos Yeroskipou | - | Enosis Neon Paralimni | 0:0 | ||
| R (match retour) | Enosis Neon Paralimni | - | Atromitos Yeroskipou | 3:0 | ||
| H (Match allé): 21.01.2009 16:00 | R (match retour): 04.02.2009 14:00 | vainqueur: Enosis Neon Paralimni | ||||
| H (Match allé) | Anorthosis Famagusta | - | Apollon Limassol | 2:1 | ||
| R (match retour) | Apollon Limassol | - | Anorthosis Famagusta | 3:1 ap | ||
| H (Match allé): 21.01.2009 17:00 | R (match retour): 04.02.2009 17:00 | vainqueur: Apollon Limassol | ||||
