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| H | KF Shkëndija 79 | - | Vardar Skopje | 2:1 | ||
| R | Vardar Skopje | - | KF Shkëndija 79 | 3:0 (3:0) | ||
| H: 24.09.2014 15:30 | R: 22.10.2014 15:00 | Sieger: Vardar Skopje | ||||
| H | FK Miravci | - | Napredok Kičevo | 0:0 | ||
| R | Napredok Kičevo | - | FK Miravci | 1:5 (0:2) | ||
| H: 24.09.2014 15:30 | R: 14.10.2014 15:00 | Sieger: FK Miravci | ||||
| H | FK Pelister | - | FK Rabotnički | 0:0 | ||
| R | FK Rabotnički | - | FK Pelister | 3:1 (1:0) | ||
| H: 24.09.2014 15:30 | R: 21.10.2014 14:30 | Sieger: FK Rabotnički | ||||
| H | KF Gostivari | - | FK Renova | 1:4 (1:2) | ||
| R | FK Renova | - | KF Gostivari | 1:0 (1:0) | ||
| H: 24.09.2014 15:30 | R: 14.10.2014 12:00 | Sieger: FK Renova | ||||
| H | FK Viktorija | - | FK Drita | 1:0 | ||
| R | FK Drita | - | FK Viktorija | 3:1 (0:0, 1:1) i.E. | ||
| H: 24.09.2014 15:30 | R: 14.10.2014 15:00 | Sieger: FK Drita | ||||
| H | FK Turnovo | - | FK Bregalnica Štip | 0:0 | ||
| R | FK Bregalnica Štip | - | FK Turnovo | 3:4 (0:0, 0:0) i.E. | ||
| H: 24.09.2014 15:30 | R: 14.10.2014 15:00 | Sieger: FK Turnovo | ||||
| H | Sileks Kratovo | - | FK Gorno Lisiče | 1:1 | ||
| R | FK Gorno Lisiče | - | Sileks Kratovo | 0:0 (0:0) | ||
| H: 24.09.2014 15:30 | R: 14.10.2014 15:00 | Sieger: FK Gorno Lisiče | ||||
| H | KF Shkupi | - | FK Teteks | 1:1 | ||
| R | FK Teteks | - | KF Shkupi | 1:0 (1:0) | ||
| H: 24.09.2014 15:30 | R: 14.10.2014 15:00 | Sieger: FK Teteks | ||||
