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| U | FK Bregalnica Štip | - | FK Pelister | 0:0 | ||
| R | FK Pelister | - | FK Bregalnica Štip | 0:2 (0:1) | ||
| U: 15.09.2010 15:30 | R: 29.09.2010 14:30 | Winnaars: FK Bregalnica Štip | ||||
| U | Vardar Skopje | - | FK Renova | 1:1 | ||
| R | FK Renova | - | Vardar Skopje | 0:1 | ||
| U: 15.09.2010 15:30 | R: 28.09.2010 14:30 | Winnaars: Vardar Skopje | ||||
| U | Napredok Kičevo | - | FK Vlaznimi | 4:0 | ||
| R | FK Vlaznimi | - | Napredok Kičevo | 2:0 | ||
| U: 15.09.2010 15:30 | R: 29.09.2010 14:30 | Winnaars: Napredok Kičevo | ||||
| U | Sileks Kratovo | - | FK Teteks | 0:1 | ||
| R | FK Teteks | - | Sileks Kratovo | 2:0 (2:0) | ||
| U: 15.09.2010 15:30 | R: 29.09.2010 14:30 | Winnaars: FK Teteks | ||||
| U | 11 Oktomvri | - | Metalurg Skopje | 1:0 | ||
| R | Metalurg Skopje | - | 11 Oktomvri | 7:6 (0:0, 1:0, 1:0) d.p. | ||
| U: 15.09.2010 15:30 | R: 09.10.2010 14:00 | Winnaars: Metalurg Skopje | ||||
| U | Lokomotiva Skopje | - | FK Miravci | 0:0 | ||
| R | FK Miravci | - | Lokomotiva Skopje | 3:4 (0:0, 0:0, 0:0) d.p. | ||
| U: 15.09.2010 15:30 | R: 10.10.2010 14:00 | Winnaars: Lokomotiva Skopje | ||||
| U | FK Osogovo | - | GFK Tikvesh | 0:3 | ||
| R | GFK Tikvesh | - | FK Osogovo | 0:1 | ||
| U: 15.09.2010 15:30 | R: 29.09.2010 14:30 | Winnaars: GFK Tikvesh | ||||
| U | KF Gostivari | - | FK Turnovo | 0:3 | ||
| R | FK Turnovo | - | KF Gostivari | 1:0 | ||
| U: 15.09.2010 15:30 | R: 28.09.2010 14:30 | Winnaars: FK Turnovo | ||||
