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| H | Omonia Nikosia | - | APOP Kinyras | 0:0 | ||
| R | APOP Kinyras | - | Omonia Nikosia | 3:0 | ||
| H: 25.02.2009 15:00 | R: 11.03.2009 15:00 | Sieger: APOP Kinyras | ||||
| H | Ethnikos Achna | - | AEL Limassol | 1:1 | ||
| R | AEL Limassol | - | Ethnikos Achna | 2:0 | ||
| H: 25.02.2009 17:00 | R: 11.03.2009 17:00 | Sieger: AEL Limassol | ||||
| H | Ermis Aradippou | - | APOEL Nikosia | 1:1 | ||
| R | APOEL Nikosia | - | Ermis Aradippou | 3:0 | ||
| H: 04.03.2009 15:00 | R: 18.03.2009 15:00 | Sieger: APOEL Nikosia | ||||
| H | Apollon Limassol | - | Enosis Neon Paralimni | 2:1 | ||
| R | Enosis Neon Paralimni | - | Apollon Limassol | 3:2 | ||
| H: 04.03.2009 17:00 | R: 18.03.2009 17:00 | Sieger: Apollon Limassol | ||||
