Omonia Aradippou 1-7 AE Paphos
| 30.09.2009 | AE Paphos | 7-0 | Omonia Aradippou | |
| 23.09.2009 | Omonia Aradippou | 1-0 | AE Paphos | |
Frenaros 2-5 AEK Larnaca
| 30.09.2009 | AEK Larnaca | 3-0 | Frenaros | |
| 23.09.2009 | Frenaros | 2-2 | AEK Larnaca | |
Alki Larnaca 1-1 Ethnikos Achnas
| 30.09.2009 | Ethnikos Achnas | 0-0 | Alki Larnaca | |
| 23.09.2009 | Alki Larnaca | 1-1 | Ethnikos Achnas | |
Othellos Athienou 1-8 Anorthosis FC
| 30.09.2009 | Anorthosis FC | 5-1 | Othellos Athienou | |
| 23.09.2009 | Othellos Athienou | 0-3 | Anorthosis FC | |
Atromitos Yeroskipou 2-6 Ermis Aradippou
| 21.10.2009 | Ermis Aradippou | 4-0 | Atromitos Yeroskipou | |
| 30.09.2009 | Atromitos Yeroskipou | 2-2 | Ermis Aradippou | |
Ayia Napa 2-0 PAEEK Kyrenia
| 30.09.2009 | PAEEK Kyrenia | 0-0 | Ayia Napa | |
| 23.09.2009 | Ayia Napa | 2-0 | PAEEK Kyrenia | |
Digenis Morfou 1-2 Nea Salamina
| 30.09.2009 | Nea Salamina | 1-0 | Digenis Morfou | |
| 23.09.2009 | Digenis Morfou | 1-1 | Nea Salamina | |
Akritas Chlorakas 0-3 EN Paralimni
| 21.10.2009 | EN Paralimni | 3-0 | Akritas Chlorakas | |
| 23.09.2009 | Akritas Chlorakas | 0-0 | EN Paralimni | |
MEAP Nisou 1-2 Doxa Katokopia
| 30.09.2009 | Doxa Katokopia | 0-1 | MEAP Nisou | |
| 23.09.2009 | MEAP Nisou | 0-2 | Doxa Katokopia | |
Olympiakos Nicosia 2-8 Omonia Nicosia
| 28.10.2009 | Omonia Nicosia | 5-1 | Olympiakos Nicosia | |
| 23.09.2009 | Olympiakos Nicosia | 1-3 | Omonia Nicosia | |
Onisilos Sotiras* 1-3 Aris Limassol
| 21.10.2009 | Aris Limassol | 1-0 | Onisilos Sotiras* | |
| 30.09.2009 | Onisilos Sotiras* | 1-2 | Aris Limassol | |