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| H | Ethnikos Assias | - | ASIL Lysi | 0:0 | ||
| R | ASIL Lysi | - | Ethnikos Assias | 0:2 | ||
| H: 23.09.2008 15:00 | R: 04.10.2008 15:00 | Sieger: Ethnikos Assias | ||||
| H | Ermis Aradippou | - | APEP Pitsilias | 1:1 | ||
| R | APEP Pitsilias | - | Ermis Aradippou | 2:2 n.V. | ||
| H: 23.09.2008 15:00 | R: 05.10.2008 15:00 | Sieger: Ermis Aradippou | ||||
| H | PAEEK | - | Atromitos Yeroskipou | 0:2 | ||
| R | Atromitos Yeroskipou | - | PAEEK | 0:0 | ||
| H: 24.09.2008 15:00 | R: 04.10.2008 15:00 | Sieger: Atromitos Yeroskipou | ||||
| H | Onisilos Sotiras | - | ENTHOI Lakatamia | 0:1 | ||
| R | ENTHOI Lakatamia | - | Onisilos Sotiras | 1:1 | ||
| H: 24.09.2008 15:00 | R: 04.10.2008 15:00 | Sieger: ENTHOI Lakatamia | ||||
| H | Nea Salamina | - | Doxa Katokopias | 1:3 | ||
| R | Doxa Katokopias | - | Nea Salamina | 1:1 | ||
| H: 24.09.2008 15:00 | R: 04.10.2008 15:00 | Sieger: Doxa Katokopias | ||||
| H | MEAP Nisou | - | AEK Larnaca | 0:1 | ||
| R | AEK Larnaca | - | MEAP Nisou | 3:0 | ||
| H: 24.09.2008 15:00 | R: 04.10.2008 15:00 | Sieger: AEK Larnaca | ||||
| H | Chalkanoras Idaliou | - | Enosis Neon Paralimni | 2:3 | ||
| R | Enosis Neon Paralimni | - | Chalkanoras Idaliou | 0:0 | ||
| H: 24.09.2008 15:00 | R: 04.10.2008 15:00 | Sieger: Enosis Neon Paralimni | ||||
| H | Aris Limassol | - | AE Paphos | 1:1 | ||
| R | AE Paphos | - | Aris Limassol | 1:0 | ||
| H: 24.09.2008 15:00 | R: 05.10.2008 15:00 | Sieger: AE Paphos | ||||
| H | Olympiakos Nikosia | - | AEL Limassol | 0:3 | ||
| R | AEL Limassol | - | Olympiakos Nikosia | 3:2 | ||
| H: 24.09.2008 18:00 | R: 04.10.2008 15:00 | Sieger: AEL Limassol | ||||
| H | AO Agia Napa | - | Ethnikos Achna | 2:2 | ||
| R | Ethnikos Achna | - | AO Agia Napa | 3:0 | ||
| H: 01.10.2008 15:00 | R: 05.10.2008 15:00 | Sieger: Ethnikos Achna | ||||
| H | Omonia Aradippou | - | APOP Kinyras | 0:2 | ||
| R | APOP Kinyras | - | Omonia Aradippou | 1:2 | ||
| H: 01.10.2008 15:00 | R: 05.10.2008 15:00 | Sieger: APOP Kinyras | ||||
| H | Dighenis Morphou | - | Alki Larnaca | 3:3 | ||
| R | Alki Larnaca | - | Dighenis Morphou | 1:2 | ||
| H: 01.10.2008 15:00 | R: 05.10.2008 18:00 | Sieger: Dighenis Morphou | ||||
