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| 1st(1st leg) | Ethnikos Assias | - | ASIL Lysi | 0:0 | ||
| 2nd (2nd leg) | ASIL Lysi | - | Ethnikos Assias | 0:2 | ||
| 1st(1st leg): 23/09/2008 14:00 | 2nd (2nd leg): 04/10/2008 14:00 | Winner: Ethnikos Assias | ||||
| 1st(1st leg) | Ermis Aradippou | - | APEP Pitsilias | 1:1 | ||
| 2nd (2nd leg) | APEP Pitsilias | - | Ermis Aradippou | 2:2 aet | ||
| 1st(1st leg): 23/09/2008 14:00 | 2nd (2nd leg): 05/10/2008 14:00 | Winner: Ermis Aradippou | ||||
| 1st(1st leg) | PAEEK | - | Atromitos Yeroskipou | 0:2 | ||
| 2nd (2nd leg) | Atromitos Yeroskipou | - | PAEEK | 0:0 | ||
| 1st(1st leg): 24/09/2008 14:00 | 2nd (2nd leg): 04/10/2008 14:00 | Winner: Atromitos Yeroskipou | ||||
| 1st(1st leg) | Onisilos Sotiras | - | ENTHOI Lakatamia | 0:1 | ||
| 2nd (2nd leg) | ENTHOI Lakatamia | - | Onisilos Sotiras | 1:1 | ||
| 1st(1st leg): 24/09/2008 14:00 | 2nd (2nd leg): 04/10/2008 14:00 | Winner: ENTHOI Lakatamia | ||||
| 1st(1st leg) | Nea Salamina | - | Doxa Katokopias | 1:3 | ||
| 2nd (2nd leg) | Doxa Katokopias | - | Nea Salamina | 1:1 | ||
| 1st(1st leg): 24/09/2008 14:00 | 2nd (2nd leg): 04/10/2008 14:00 | Winner: Doxa Katokopias | ||||
| 1st(1st leg) | MEAP Nisou | - | AEK Larnaca | 0:1 | ||
| 2nd (2nd leg) | AEK Larnaca | - | MEAP Nisou | 3:0 | ||
| 1st(1st leg): 24/09/2008 14:00 | 2nd (2nd leg): 04/10/2008 14:00 | Winner: AEK Larnaca | ||||
| 1st(1st leg) | Chalkanoras Idaliou | - | Enosis Neon Paralimni | 2:3 | ||
| 2nd (2nd leg) | Enosis Neon Paralimni | - | Chalkanoras Idaliou | 0:0 | ||
| 1st(1st leg): 24/09/2008 14:00 | 2nd (2nd leg): 04/10/2008 14:00 | Winner: Enosis Neon Paralimni | ||||
| 1st(1st leg) | Aris Limassol | - | AE Paphos | 1:1 | ||
| 2nd (2nd leg) | AE Paphos | - | Aris Limassol | 1:0 | ||
| 1st(1st leg): 24/09/2008 14:00 | 2nd (2nd leg): 05/10/2008 14:00 | Winner: AE Paphos | ||||
| 1st(1st leg) | Olympiakos Nikosia | - | AEL Limassol | 0:3 | ||
| 2nd (2nd leg) | AEL Limassol | - | Olympiakos Nikosia | 3:2 | ||
| 1st(1st leg): 24/09/2008 17:00 | 2nd (2nd leg): 04/10/2008 14:00 | Winner: AEL Limassol | ||||
| 1st(1st leg) | AO Agia Napa | - | Ethnikos Achna | 2:2 | ||
| 2nd (2nd leg) | Ethnikos Achna | - | AO Agia Napa | 3:0 | ||
| 1st(1st leg): 01/10/2008 14:00 | 2nd (2nd leg): 05/10/2008 14:00 | Winner: Ethnikos Achna | ||||
| 1st(1st leg) | Omonia Aradippou | - | APOP Kinyras | 0:2 | ||
| 2nd (2nd leg) | APOP Kinyras | - | Omonia Aradippou | 1:2 | ||
| 1st(1st leg): 01/10/2008 14:00 | 2nd (2nd leg): 05/10/2008 14:00 | Winner: APOP Kinyras | ||||
| 1st(1st leg) | Dighenis Morphou | - | Alki Larnaca | 3:3 | ||
| 2nd (2nd leg) | Alki Larnaca | - | Dighenis Morphou | 1:2 | ||
| 1st(1st leg): 01/10/2008 14:00 | 2nd (2nd leg): 05/10/2008 17:00 | Winner: Dighenis Morphou | ||||
