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| H | Dighenis Morphou | - | Nea Salamina | 1:1 | ||
| R | Nea Salamina | - | Dighenis Morphou | 1:0 | ||
| H: 23.09.2009 15:00 | R: 30.09.2009 14:30 | Sieger: Nea Salamina | ||||
| H | MEAP Nisou | - | Doxa Katokopias | 0:2 | ||
| R | Doxa Katokopias | - | MEAP Nisou | 0:1 | ||
| H: 23.09.2009 15:00 | R: 30.09.2009 14:30 | Sieger: Doxa Katokopias | ||||
| H | Alki Larnaca | - | Ethnikos Achna | 1:1 | ||
| R | Ethnikos Achna | - | Alki Larnaca | 0:0 | ||
| H: 23.09.2009 15:00 | R: 30.09.2009 18:00 | Sieger: Ethnikos Achna | ||||
| H | ASIL Lysi | - | APEP Pitsilias | 0:3 | ||
| R | APEP Pitsilias | - | ASIL Lysi | 1:2 | ||
| H: 23.09.2009 15:00 | R: 28.10.2009 14:00 | Sieger: APEP Pitsilias | ||||
| H | AO Agia Napa | - | PAEEK | 2:0 | ||
| R | PAEEK | - | AO Agia Napa | 0:0 | ||
| H: 23.09.2009 15:00 | R: 30.09.2009 14:30 | Sieger: AO Agia Napa | ||||
| H | Omonia Aradippou | - | AE Paphos | 1:0 | ||
| R | AE Paphos | - | Omonia Aradippou | 7:0 | ||
| H: 23.09.2009 15:00 | R: 30.09.2009 14:30 | Sieger: AE Paphos | ||||
| H | Frenaros FC 2000 | - | AEK Larnaca | 2:2 | ||
| R | AEK Larnaca | - | Frenaros FC 2000 | 3:0 | ||
| H: 23.09.2009 15:00 | R: 30.09.2009 14:30 | Sieger: AEK Larnaca | ||||
| H | Akritas Chlorakas | - | Enosis Neon Paralimni | 0:0 | ||
| R | Enosis Neon Paralimni | - | Akritas Chlorakas | 3:0 | ||
| H: 23.09.2009 15:00 | R: 21.10.2009 15:00 | Sieger: Enosis Neon Paralimni | ||||
| H | Othellos Athienou | - | Anorthosis Famagusta | 0:3 | ||
| R | Anorthosis Famagusta | - | Othellos Athienou | 5:1 | ||
| H: 23.09.2009 15:00 | R: 30.09.2009 17:00 | Sieger: Anorthosis Famagusta | ||||
| H | Olympiakos Nikosia | - | Omonia Nikosia | 1:3 | ||
| R | Omonia Nikosia | - | Olympiakos Nikosia | 5:1 | ||
| H: 23.09.2009 18:00 | R: 28.10.2009 17:00 | Sieger: Omonia Nikosia | ||||
| H | Onisilos Sotiras | - | Aris Limassol | 1:2 | ||
| R | Aris Limassol | - | Onisilos Sotiras | 1:0 | ||
| H: 30.09.2009 14:30 | R: 21.10.2009 15:00 | Sieger: Aris Limassol | ||||
| H | Atromitos Yeroskipou | - | Ermis Aradippou | 2:2 | ||
| R | Ermis Aradippou | - | Atromitos Yeroskipou | 4:0 | ||
| H: 30.09.2009 15:00 | R: 21.10.2009 17:00 | Sieger: Ermis Aradippou | ||||
