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| 1st(1st leg) | Dighenis Morphou | - | Nea Salamina | 1:1 | ||
| 2nd (2nd leg) | Nea Salamina | - | Dighenis Morphou | 1:0 | ||
| 1st(1st leg): 23/09/2009 14:00 | 2nd (2nd leg): 30/09/2009 13:30 | Winner: Nea Salamina | ||||
| 1st(1st leg) | MEAP Nisou | - | Doxa Katokopias | 0:2 | ||
| 2nd (2nd leg) | Doxa Katokopias | - | MEAP Nisou | 0:1 | ||
| 1st(1st leg): 23/09/2009 14:00 | 2nd (2nd leg): 30/09/2009 13:30 | Winner: Doxa Katokopias | ||||
| 1st(1st leg) | Alki Larnaca | - | Ethnikos Achna | 1:1 | ||
| 2nd (2nd leg) | Ethnikos Achna | - | Alki Larnaca | 0:0 | ||
| 1st(1st leg): 23/09/2009 14:00 | 2nd (2nd leg): 30/09/2009 17:00 | Winner: Ethnikos Achna | ||||
| 1st(1st leg) | ASIL Lysi | - | APEP Pitsilias | 0:3 | ||
| 2nd (2nd leg) | APEP Pitsilias | - | ASIL Lysi | 1:2 | ||
| 1st(1st leg): 23/09/2009 14:00 | 2nd (2nd leg): 28/10/2009 13:00 | Winner: APEP Pitsilias | ||||
| 1st(1st leg) | AO Agia Napa | - | PAEEK | 2:0 | ||
| 2nd (2nd leg) | PAEEK | - | AO Agia Napa | 0:0 | ||
| 1st(1st leg): 23/09/2009 14:00 | 2nd (2nd leg): 30/09/2009 13:30 | Winner: AO Agia Napa | ||||
| 1st(1st leg) | Omonia Aradippou | - | AE Paphos | 1:0 | ||
| 2nd (2nd leg) | AE Paphos | - | Omonia Aradippou | 7:0 | ||
| 1st(1st leg): 23/09/2009 14:00 | 2nd (2nd leg): 30/09/2009 13:30 | Winner: AE Paphos | ||||
| 1st(1st leg) | Frenaros FC 2000 | - | AEK Larnaca | 2:2 | ||
| 2nd (2nd leg) | AEK Larnaca | - | Frenaros FC 2000 | 3:0 | ||
| 1st(1st leg): 23/09/2009 14:00 | 2nd (2nd leg): 30/09/2009 13:30 | Winner: AEK Larnaca | ||||
| 1st(1st leg) | Akritas Chlorakas | - | Enosis Neon Paralimni | 0:0 | ||
| 2nd (2nd leg) | Enosis Neon Paralimni | - | Akritas Chlorakas | 3:0 | ||
| 1st(1st leg): 23/09/2009 14:00 | 2nd (2nd leg): 21/10/2009 14:00 | Winner: Enosis Neon Paralimni | ||||
| 1st(1st leg) | Othellos Athienou | - | Anorthosis Famagusta | 0:3 | ||
| 2nd (2nd leg) | Anorthosis Famagusta | - | Othellos Athienou | 5:1 | ||
| 1st(1st leg): 23/09/2009 14:00 | 2nd (2nd leg): 30/09/2009 16:00 | Winner: Anorthosis Famagusta | ||||
| 1st(1st leg) | Olympiakos Nikosia | - | Omonia Nikosia | 1:3 | ||
| 2nd (2nd leg) | Omonia Nikosia | - | Olympiakos Nikosia | 5:1 | ||
| 1st(1st leg): 23/09/2009 17:00 | 2nd (2nd leg): 28/10/2009 16:00 | Winner: Omonia Nikosia | ||||
| 1st(1st leg) | Onisilos Sotiras | - | Aris Limassol | 1:2 | ||
| 2nd (2nd leg) | Aris Limassol | - | Onisilos Sotiras | 1:0 | ||
| 1st(1st leg): 30/09/2009 13:30 | 2nd (2nd leg): 21/10/2009 14:00 | Winner: Aris Limassol | ||||
| 1st(1st leg) | Atromitos Yeroskipou | - | Ermis Aradippou | 2:2 | ||
| 2nd (2nd leg) | Ermis Aradippou | - | Atromitos Yeroskipou | 4:0 | ||
| 1st(1st leg): 30/09/2009 14:00 | 2nd (2nd leg): 21/10/2009 16:00 | Winner: Ermis Aradippou | ||||
