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| H | Aris Limassol | - | AEK Larnaca | 0:0 | ||
| R | AEK Larnaca | - | Aris Limassol | 0:1 | ||
| H: 25.11.2009 15:00 | R: 02.12.2009 16:30 | Sieger: Aris Limassol | ||||
| H | Anorthosis Famagusta | - | AO Agia Napa | 6:0 | ||
| R | AO Agia Napa | - | Anorthosis Famagusta | 2:1 | ||
| H: 25.11.2009 15:00 | R: 09.12.2009 13:30 | Sieger: Anorthosis Famagusta | ||||
| H | APOP Kinyras | - | AE Paphos | 4:1 | ||
| R | AE Paphos | - | APOP Kinyras | 4:2 | ||
| H: 25.11.2009 17:00 | R: 02.12.2009 17:00 | Sieger: APOP Kinyras | ||||
| H | Ermis Aradippou | - | Enosis Neon Paralimni | 4:0 | ||
| R | Enosis Neon Paralimni | - | Ermis Aradippou | 2:0 | ||
| H: 25.11.2009 17:00 | R: 02.12.2009 15:00 | Sieger: Ermis Aradippou | ||||
| H | APEP Pitsilias | - | Doxa Katokopias | 1:1 | ||
| R | Doxa Katokopias | - | APEP Pitsilias | 0:1 | ||
| H: 02.12.2009 15:00 | R: 16.12.2009 13:30 | Sieger: APEP Pitsilias | ||||
| H | AEL Limassol | - | Omonia Nikosia | 0:1 | ||
| R | Omonia Nikosia | - | AEL Limassol | 0:2 | ||
| H: 09.12.2009 13:30 | R: 16.12.2009 13:30 | Sieger: AEL Limassol | ||||
| H | Nea Salamina | - | Apollon Limassol | 1:0 | ||
| R | Apollon Limassol | - | Nea Salamina | 2:0 | ||
| H: 09.12.2009 15:00 | R: 16.12.2009 17:00 | Sieger: Apollon Limassol | ||||
| H | APOEL Nikosia | - | Ethnikos Achna | 0:2 | ||
| R | Ethnikos Achna | - | APOEL Nikosia | 0:4 n.V. | ||
| H: 06.01.2010 15:00 | R: 27.01.2010 18:00 | Sieger: APOEL Nikosia | ||||
