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| 1st(1st leg) | KF Shkëndija 79 | - | Vardar Skopje | 2:1 | ||
| 2nd (2nd leg) | Vardar Skopje | - | KF Shkëndija 79 | 3:0 (3:0) | ||
| 1st(1st leg): 24/09/2014 14:30 | 2nd (2nd leg): 22/10/2014 14:00 | Winner: Vardar Skopje | ||||
| 1st(1st leg) | FK Miravci | - | Napredok Kičevo | 0:0 | ||
| 2nd (2nd leg) | Napredok Kičevo | - | FK Miravci | 1:5 (0:2) | ||
| 1st(1st leg): 24/09/2014 14:30 | 2nd (2nd leg): 14/10/2014 14:00 | Winner: FK Miravci | ||||
| 1st(1st leg) | FK Pelister | - | FK Rabotnički | 0:0 | ||
| 2nd (2nd leg) | FK Rabotnički | - | FK Pelister | 3:1 (1:0) | ||
| 1st(1st leg): 24/09/2014 14:30 | 2nd (2nd leg): 21/10/2014 13:30 | Winner: FK Rabotnički | ||||
| 1st(1st leg) | KF Gostivari | - | FK Renova | 1:4 (1:2) | ||
| 2nd (2nd leg) | FK Renova | - | KF Gostivari | 1:0 (1:0) | ||
| 1st(1st leg): 24/09/2014 14:30 | 2nd (2nd leg): 14/10/2014 11:00 | Winner: FK Renova | ||||
| 1st(1st leg) | FK Viktorija | - | FK Drita | 1:0 | ||
| 2nd (2nd leg) | FK Drita | - | FK Viktorija | 3:1 (0:0, 1:1) pso | ||
| 1st(1st leg): 24/09/2014 14:30 | 2nd (2nd leg): 14/10/2014 14:00 | Winner: FK Drita | ||||
| 1st(1st leg) | FK Turnovo | - | FK Bregalnica Štip | 0:0 | ||
| 2nd (2nd leg) | FK Bregalnica Štip | - | FK Turnovo | 3:4 (0:0, 0:0) pso | ||
| 1st(1st leg): 24/09/2014 14:30 | 2nd (2nd leg): 14/10/2014 14:00 | Winner: FK Turnovo | ||||
| 1st(1st leg) | Sileks Kratovo | - | FK Gorno Lisiče | 1:1 | ||
| 2nd (2nd leg) | FK Gorno Lisiče | - | Sileks Kratovo | 0:0 (0:0) | ||
| 1st(1st leg): 24/09/2014 14:30 | 2nd (2nd leg): 14/10/2014 14:00 | Winner: FK Gorno Lisiče | ||||
| 1st(1st leg) | KF Shkupi | - | FK Teteks | 1:1 | ||
| 2nd (2nd leg) | FK Teteks | - | KF Shkupi | 1:0 (1:0) | ||
| 1st(1st leg): 24/09/2014 14:30 | 2nd (2nd leg): 14/10/2014 14:00 | Winner: FK Teteks | ||||
