Jaish Damascus 1-2 Ittihad Aleppo *
| 29.05.2009 | Ittihad Aleppo | 2-1 | Jaish Damascus | |
| 22.05.2009 | Jaish Damascus | 0-0 | Ittihad Aleppo | |
Taliya Hama 2-3 Karamah *
| 07.06.2009 | Karamah | 2-0 | Taliya Hama | |
| 31.05.2009 | Taliya Hama | 2-1 | Karamah | |
*Majd Damascus 4-3 Afrin SC
| 07.06.2009 | Afrin SC | 2-0 | Majd Damascus | |
| 30.05.2009 | Majd Damascus | 4-1 | Afrin SC | |
Shorta Damascus 4-4 Wathba Homs *
| 29.05.2009 | Wathba Homs | 2-0 | Shorta Damascus | |
| 22.05.2009 | Shorta Damascus | 4-2 | Wathba Homs | |