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| U | FK Bregalnica Štip | - | KF Shkëndija 79 | 2:1 | ||
| R | KF Shkëndija 79 | - | FK Bregalnica Štip | 1:1 | ||
| U: 12.10.2013 14:00 | R: 20.11.2013 13:00 | Winnaars: FK Bregalnica Štip | ||||
| U | FK Pelister | - | FK Rabotnički | 1:0 | ||
| R | FK Rabotnički | - | FK Pelister | 2:0 | ||
| U: 13.10.2013 14:00 | R: 04.12.2013 13:00 | Winnaars: FK Rabotnički | ||||
| U | FK Teteks | - | Napredok Kičevo | 0:0 | ||
| R | Napredok Kičevo | - | FK Teteks | 1:2 | ||
| U: 13.10.2013 14:00 | R: 20.11.2013 13:00 | Winnaars: FK Teteks | ||||
| U | FK Drita | - | Metalurg Skopje | 0:3 | ||
| R | Metalurg Skopje | - | FK Drita | 7:1 | ||
| U: 13.10.2013 14:00 | R: 20.11.2013 13:00 | Winnaars: Metalurg Skopje | ||||
