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| U | FK Skopje | - | 11 Oktomvri | 3:1 | ||
| R | 11 Oktomvri | - | FK Skopje | 1:0 | ||
| U: 22.09.2009 15:00 | R: 30.09.2009 15:00 | Winnaars: FK Skopje | ||||
| U | FK Pelister | - | FK Ohrid | 2:0 | ||
| R | FK Ohrid | - | FK Pelister | 0:3 | ||
| U: 23.09.2009 15:00 | R: 30.09.2009 | Winnaars: FK Pelister | ||||
| U | Lokomotiva Skopje | - | FK Renova | 0:3 | ||
| R | FK Renova | - | Lokomotiva Skopje | 3:0 | ||
| U: 23.09.2009 15:00 | R: 30.09.2009 15:00 | Winnaars: FK Renova | ||||
| U | Metalurg Skopje | - | FK Pobeda | 1:0 | ||
| R | FK Pobeda | - | Metalurg Skopje | 3:4 d.p. | ||
| U: 23.09.2009 15:00 | R: 30.09.2009 15:00 | Winnaars: Metalurg Skopje | ||||
| U | FK Vlazrimi 77 | - | FK Drita | 0:1 | ||
| R | FK Drita | - | FK Vlazrimi 77 | 1:1 | ||
| U: 23.09.2009 15:00 | R: 30.09.2009 15:00 | Winnaars: FK Drita | ||||
| U | FK Belasica | - | FK Teteks | 1:3 | ||
| R | FK Teteks | - | FK Belasica | 1:0 | ||
| U: 23.09.2009 15:00 | R: 30.09.2009 15:00 | Winnaars: FK Teteks | ||||
| U | Sileks Kratovo | - | Makedonija GP | 1:1 | ||
| R | Makedonija GP | - | Sileks Kratovo | 2:1 | ||
| U: 23.09.2009 15:00 | R: 30.09.2009 15:00 | Winnaars: Makedonija GP | ||||
| U | FK Fortuna | - | FK Rabotnički | 0:6 | ||
| R | FK Rabotnički | - | FK Fortuna | 3:0 | ||
| U: 23.09.2009 15:00 | R: 30.09.2009 | Winnaars: FK Rabotnički | ||||
