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| U | FK Renova | - | KF Gostivari | 0:1 (0:0) | ||
| R | KF Gostivari | - | FK Renova | 1:5 (0:3) | ||
| U: 13.09.2011 15:30 | R: 28.09.2011 14:30 | Winnaars: FK Renova | ||||
| U | Sileks Kratovo | - | FK Teteks | 2:2 (1:1) | ||
| R | FK Teteks | - | Sileks Kratovo | 0:0 (0:0) | ||
| U: 14.09.2011 15:30 | R: 28.09.2011 14:30 | Winnaars: FK Teteks | ||||
| U | 11 Oktomvri | - | FK Skopje | 4:0 (3:0) | ||
| R | FK Skopje | - | 11 Oktomvri | 2:0 (0:0) | ||
| U: 14.09.2011 15:30 | R: 29.09.2011 14:30 | Winnaars: 11 Oktomvri | ||||
| U | KF Shkëndija 79 | - | FK Bregalnica Štip | 2:0 (0:0) | ||
| R | FK Bregalnica Štip | - | KF Shkëndija 79 | 3:0 (1:0, 2:0) d.p. | ||
| U: 14.09.2011 15:30 | R: 28.09.2011 14:30 | Winnaars: FK Bregalnica Štip | ||||
| U | FK Turnovo | - | FK Pelister | 1:0 | ||
| R | FK Pelister | - | FK Turnovo | 1:1 (0:0) | ||
| U: 14.09.2011 15:30 | R: 28.09.2011 14:30 | Winnaars: FK Turnovo | ||||
| U | Napredok Kičevo | - | FK Miravci | 3:1 (2:0) | ||
| R | FK Miravci | - | Napredok Kičevo | 2:3 | ||
| U: 14.09.2011 15:30 | R: 28.09.2011 14:30 | Winnaars: Napredok Kičevo | ||||
| U | FK Rabotnički | - | Metalurg Skopje | 0:0 | ||
| R | Metalurg Skopje | - | FK Rabotnički | 3:5 (0:0, 0:0) d.p. | ||
| U: 14.09.2011 15:30 | R: 28.09.2011 14:30 | Winnaars: FK Rabotnički | ||||
| U | Vardar Skopje | - | GFK Tikvesh | 6:1 (4:1) | ||
| R | GFK Tikvesh | - | Vardar Skopje | 0:1 (0:0) | ||
| U: 15.09.2011 18:30 | R: 28.09.2011 14:30 | Winnaars: Vardar Skopje | ||||
