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GMT 01:00
| 05.10.2008 | |||
| 18:00 | Alki Larnaca | 1-2 | Digenis Morfou |
| 15:00 | APEP FC | 2-2 AET | Ermis Aradippou |
| 15:00 | APOP FC | 1-2 | Omonia Aradippou |
| 15:00 | Atromitos Yeroskipou | 3-1 | PAEEK Kyrenia |
| 15:00 | Ethnikos Achnas | 3-0 | Ayia Napa |
| 04.10.2008 | |||
| 19:00 | AE Paphos | 1-0 | Aris Limassol |
| 15:00 | AEK Larnaca | 3-0 | MEAP Nisou |
| 15:00 | AEL Limassol | 3-2 | Olympiakos Nicosia |
| 15:00 | ASIL Lysi | 0-2 | Ethnikos Assia |
| 15:00 | Doxa Katokopia | 1-1 | Nea Salamina |
| 15:00 | EN Paralimni | 0-0 | Halkanoras Idaliou |
| 15:00 | EN THOI Lakatamia | 1-1 | Onisilos Sotiras* |
| 01.10.2008 | |||
| 15:10 | Digenis Morfou | 4-3 | Alki Larnaca |
| 15:00 | Ayia Napa | 2-2 | Ethnikos Achnas |
| 15:00 | Omonia Aradippou | 0-2 | APOP FC |
| 24.09.2008 | |||
| 18:00 | Olympiakos Nicosia | 0-3 | AEL Limassol |
| 15:00 | Aris Limassol | 1-1 | AE Paphos |
| 15:00 | Halkanoras Idaliou | 2-3 | EN Paralimni |
| 15:00 | MEAP Nisou | 0-1 | AEK Larnaca |
| 15:00 | Nea Salamina | 1-3 | Doxa Katokopia |
| 15:00 | Onisilos Sotiras* | 0-1 | EN THOI Lakatamia |
| 15:00 | PAEEK Kyrenia | 0-2 | Atromitos Yeroskipou |
| 23.09.2008 | |||
| 15:00 | Ermis Aradippou | 1-1 | APEP FC |
| 15:00 | Ethnikos Assia | 0-0 | ASIL Lysi |
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