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| 1st(1st leg) | FK Bregalnica Štip | - | FK Pelister | 0:0 | ||
| 2nd (2nd leg) | FK Pelister | - | FK Bregalnica Štip | 0:2 (0:1) | ||
| 1st(1st leg): 15/09/2010 14:30 | 2nd (2nd leg): 29/09/2010 13:30 | Winner: FK Bregalnica Štip | ||||
| 1st(1st leg) | Vardar Skopje | - | FK Renova | 1:1 | ||
| 2nd (2nd leg) | FK Renova | - | Vardar Skopje | 0:1 | ||
| 1st(1st leg): 15/09/2010 14:30 | 2nd (2nd leg): 28/09/2010 13:30 | Winner: Vardar Skopje | ||||
| 1st(1st leg) | Napredok Kičevo | - | FK Vlaznimi | 4:0 | ||
| 2nd (2nd leg) | FK Vlaznimi | - | Napredok Kičevo | 2:0 | ||
| 1st(1st leg): 15/09/2010 14:30 | 2nd (2nd leg): 29/09/2010 13:30 | Winner: Napredok Kičevo | ||||
| 1st(1st leg) | Sileks Kratovo | - | FK Teteks | 0:1 | ||
| 2nd (2nd leg) | FK Teteks | - | Sileks Kratovo | 2:0 (2:0) | ||
| 1st(1st leg): 15/09/2010 14:30 | 2nd (2nd leg): 29/09/2010 13:30 | Winner: FK Teteks | ||||
| 1st(1st leg) | 11 Oktomvri | - | Metalurg Skopje | 1:0 | ||
| 2nd (2nd leg) | Metalurg Skopje | - | 11 Oktomvri | 7:6 (0:0, 1:0, 1:0) pso | ||
| 1st(1st leg): 15/09/2010 14:30 | 2nd (2nd leg): 09/10/2010 13:00 | Winner: Metalurg Skopje | ||||
| 1st(1st leg) | Lokomotiva Skopje | - | FK Miravci | 0:0 | ||
| 2nd (2nd leg) | FK Miravci | - | Lokomotiva Skopje | 3:4 (0:0, 0:0, 0:0) pso | ||
| 1st(1st leg): 15/09/2010 14:30 | 2nd (2nd leg): 10/10/2010 13:00 | Winner: Lokomotiva Skopje | ||||
| 1st(1st leg) | FK Osogovo | - | GFK Tikvesh | 0:3 | ||
| 2nd (2nd leg) | GFK Tikvesh | - | FK Osogovo | 0:1 | ||
| 1st(1st leg): 15/09/2010 14:30 | 2nd (2nd leg): 29/09/2010 13:30 | Winner: GFK Tikvesh | ||||
| 1st(1st leg) | KF Gostivari | - | FK Turnovo | 0:3 | ||
| 2nd (2nd leg) | FK Turnovo | - | KF Gostivari | 1:0 | ||
| 1st(1st leg): 15/09/2010 14:30 | 2nd (2nd leg): 28/09/2010 13:30 | Winner: FK Turnovo | ||||
