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| 1st(1st leg) | FK Skopje | - | 11 Oktomvri | 3:1 | ||
| 2nd (2nd leg) | 11 Oktomvri | - | FK Skopje | 1:0 | ||
| 1st(1st leg): 22/09/2009 14:00 | 2nd (2nd leg): 30/09/2009 14:00 | Winner: FK Skopje | ||||
| 1st(1st leg) | FK Pelister | - | FK Ohrid | 2:0 | ||
| 2nd (2nd leg) | FK Ohrid | - | FK Pelister | 0:3 | ||
| 1st(1st leg): 23/09/2009 14:00 | 2nd (2nd leg): 30/09/2009 | Winner: FK Pelister | ||||
| 1st(1st leg) | Lokomotiva Skopje | - | FK Renova | 0:3 | ||
| 2nd (2nd leg) | FK Renova | - | Lokomotiva Skopje | 3:0 | ||
| 1st(1st leg): 23/09/2009 14:00 | 2nd (2nd leg): 30/09/2009 14:00 | Winner: FK Renova | ||||
| 1st(1st leg) | Metalurg Skopje | - | FK Pobeda | 1:0 | ||
| 2nd (2nd leg) | FK Pobeda | - | Metalurg Skopje | 3:4 pso | ||
| 1st(1st leg): 23/09/2009 14:00 | 2nd (2nd leg): 30/09/2009 14:00 | Winner: Metalurg Skopje | ||||
| 1st(1st leg) | FK Vlazrimi 77 | - | FK Drita | 0:1 | ||
| 2nd (2nd leg) | FK Drita | - | FK Vlazrimi 77 | 1:1 | ||
| 1st(1st leg): 23/09/2009 14:00 | 2nd (2nd leg): 30/09/2009 14:00 | Winner: FK Drita | ||||
| 1st(1st leg) | FK Belasica | - | FK Teteks | 1:3 | ||
| 2nd (2nd leg) | FK Teteks | - | FK Belasica | 1:0 | ||
| 1st(1st leg): 23/09/2009 14:00 | 2nd (2nd leg): 30/09/2009 14:00 | Winner: FK Teteks | ||||
| 1st(1st leg) | Sileks Kratovo | - | Makedonija GP | 1:1 | ||
| 2nd (2nd leg) | Makedonija GP | - | Sileks Kratovo | 2:1 | ||
| 1st(1st leg): 23/09/2009 14:00 | 2nd (2nd leg): 30/09/2009 14:00 | Winner: Makedonija GP | ||||
| 1st(1st leg) | FK Fortuna | - | FK Rabotnički | 0:6 | ||
| 2nd (2nd leg) | FK Rabotnički | - | FK Fortuna | 3:0 | ||
| 1st(1st leg): 23/09/2009 14:00 | 2nd (2nd leg): 30/09/2009 | Winner: FK Rabotnički | ||||
