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| 1st(1st leg) | FK Pelister | - | FK Drita | 2:2 | ||
| 2nd (2nd leg) | FK Drita | - | FK Pelister | 0:1 | ||
| 1st(1st leg): 28/10/2009 12:00 | 2nd (2nd leg): 25/11/2009 12:00 | Winner: FK Pelister | ||||
| 1st(1st leg) | FK Rabotnički | - | FK Renova | 4:0 | ||
| 2nd (2nd leg) | FK Renova | - | FK Rabotnički | 0:1 | ||
| 1st(1st leg): 28/10/2009 12:00 | 2nd (2nd leg): 25/11/2009 12:00 | Winner: FK Rabotnički | ||||
| 1st(1st leg) | Makedonija GP | - | FK Teteks | 2:0 | ||
| 2nd (2nd leg) | FK Teteks | - | Makedonija GP | 3:0 | ||
| 1st(1st leg): 28/10/2009 12:00 | 2nd (2nd leg): 26/11/2009 12:00 | Winner: FK Teteks | ||||
| 1st(1st leg) | FK Skopje | - | Metalurg Skopje | 0:0 | ||
| 2nd (2nd leg) | Metalurg Skopje | - | FK Skopje | 2:2 | ||
| 1st(1st leg): 28/10/2009 12:00 | 2nd (2nd leg): 25/11/2009 12:00 | Winner: FK Skopje | ||||
