Aris Limassol 1-2 AE Paphos
| 04.10.2008 | AE Paphos | 1-0 | Aris Limassol | |
| 24.09.2008 | Aris Limassol | 1-1 | AE Paphos | |
Olympiakos Nicosia 2-6 AEL Limassol
| 04.10.2008 | AEL Limassol | 3-2 | Olympiakos Nicosia | |
| 24.09.2008 | Olympiakos Nicosia | 0-3 | AEL Limassol | |
Ermis Aradippou 3-3 APEP FC
| 05.10.2008 | APEP FC | 2-2 AET | Ermis Aradippou | |
| 23.09.2008 | Ermis Aradippou | 1-1 | APEP FC | |
Ethnikos Assia 2-0 ASIL Lysi
| 04.10.2008 | ASIL Lysi | 0-2 | Ethnikos Assia | |
| 23.09.2008 | Ethnikos Assia | 0-0 | ASIL Lysi | |
Ayia Napa 2-5 Ethnikos Achnas
| 05.10.2008 | Ethnikos Achnas | 3-0 | Ayia Napa | |
| 01.10.2008 | Ayia Napa | 2-2 | Ethnikos Achnas | |
Digenis Morfou 6-4 Alki Larnaca
| 05.10.2008 | Alki Larnaca | 1-2 | Digenis Morfou | |
| 01.10.2008 | Digenis Morfou | 4-3 | Alki Larnaca | |
Onisilos Sotiras* 1-2 EN THOI Lakatamia
| 04.10.2008 | EN THOI Lakatamia | 1-1 | Onisilos Sotiras* | |
| 24.09.2008 | Onisilos Sotiras* | 0-1 | EN THOI Lakatamia | |
Halkanoras Idaliou 2-3 EN Paralimni
| 04.10.2008 | EN Paralimni | 0-0 | Halkanoras Idaliou | |
| 24.09.2008 | Halkanoras Idaliou | 2-3 | EN Paralimni | |
MEAP Nisou 0-4 AEK Larnaca
| 04.10.2008 | AEK Larnaca | 3-0 | MEAP Nisou | |
| 24.09.2008 | MEAP Nisou | 0-1 | AEK Larnaca | |
Nea Salamina 2-4 Doxa Katokopia
| 04.10.2008 | Doxa Katokopia | 1-1 | Nea Salamina | |
| 24.09.2008 | Nea Salamina | 1-3 | Doxa Katokopia | |
Omonia Aradippou 2-3 APOP FC
| 05.10.2008 | APOP FC | 1-2 | Omonia Aradippou | |
| 01.10.2008 | Omonia Aradippou | 0-2 | APOP FC | |
PAEEK Kyrenia 1-5 Atromitos Yeroskipou
| 05.10.2008 | Atromitos Yeroskipou | 3-1 | PAEEK Kyrenia | |
| 24.09.2008 | PAEEK Kyrenia | 0-2 | Atromitos Yeroskipou | |