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| U | FK Pelister | - | FK Drita | 2:2 | ||
| R | FK Drita | - | FK Pelister | 0:1 | ||
| U: 28.10.2009 13:00 | R: 25.11.2009 13:00 | Winnaars: FK Pelister | ||||
| U | FK Rabotnički | - | FK Renova | 4:0 | ||
| R | FK Renova | - | FK Rabotnički | 0:1 | ||
| U: 28.10.2009 13:00 | R: 25.11.2009 13:00 | Winnaars: FK Rabotnički | ||||
| U | Makedonija GP | - | FK Teteks | 2:0 | ||
| R | FK Teteks | - | Makedonija GP | 3:0 | ||
| U: 28.10.2009 13:00 | R: 26.11.2009 13:00 | Winnaars: FK Teteks | ||||
| U | FK Skopje | - | Metalurg Skopje | 0:0 | ||
| R | Metalurg Skopje | - | FK Skopje | 2:2 | ||
| U: 28.10.2009 13:00 | R: 25.11.2009 13:00 | Winnaars: FK Skopje | ||||
