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| I | FK Pelister | - | FK Drita | 2:2 | ||
| V | FK Drita | - | FK Pelister | 0:1 | ||
| I: 28.10.2009 13:00 | V: 25.11.2009 13:00 | Campeones: FK Pelister | ||||
| I | FK Rabotnički | - | FK Renova | 4:0 | ||
| V | FK Renova | - | FK Rabotnički | 0:1 | ||
| I: 28.10.2009 13:00 | V: 25.11.2009 13:00 | Campeones: FK Rabotnički | ||||
| I | Makedonija GP | - | FK Teteks | 2:0 | ||
| V | FK Teteks | - | Makedonija GP | 3:0 | ||
| I: 28.10.2009 13:00 | V: 26.11.2009 13:00 | Campeones: FK Teteks | ||||
| I | FK Skopje | - | Metalurg Skopje | 0:0 | ||
| V | Metalurg Skopje | - | FK Skopje | 2:2 | ||
| I: 28.10.2009 13:00 | V: 25.11.2009 13:00 | Campeones: FK Skopje | ||||
