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| H | Metalurg Skopje | - | Vardar Skopje | 1:0 | ||
| R | Vardar Skopje | - | Metalurg Skopje | 2:1 (2:1) | ||
| H: 18.09.2013 16:00 | R: 25.09.2013 15:30 | Sieger: Metalurg Skopje | ||||
| H | FK Turnovo | - | FK Bregalnica Štip | 1:0 | ||
| R | FK Bregalnica Štip | - | FK Turnovo | 3:0 i.E. | ||
| H: 18.09.2013 16:00 | R: 25.09.2013 16:00 | Sieger: FK Bregalnica Štip | ||||
| H | FK Teteks | - | FK Renova | 2:2 | ||
| R | FK Renova | - | FK Teteks | 4:5 i.E. | ||
| H: 18.09.2013 16:00 | R: 25.09.2013 16:00 | Sieger: FK Teteks | ||||
| H | FK Pelister | - | FK Miravci | 2:0 | ||
| R | FK Miravci | - | FK Pelister | 2:3 i.E. | ||
| H: 18.09.2013 16:00 | R: 25.09.2013 16:00 | Sieger: FK Pelister | ||||
| H | FK Rabotnički | - | FK Novaci 2005 | 4:0 | ||
| R | FK Novaci 2005 | - | FK Rabotnički | 1:2 (1:1) | ||
| H: 18.09.2013 16:00 | R: 25.09.2013 15:30 | Sieger: FK Rabotnički | ||||
| H | Sileks Kratovo | - | FK Drita | 1:0 | ||
| R | FK Drita | - | Sileks Kratovo | 8:7 (1:0, 1:0) i.E. | ||
| H: 18.09.2013 16:00 | R: 25.09.2013 15:30 | Sieger: FK Drita | ||||
| H | KF Gostivari | - | Napredok Kičevo | 0:3 | ||
| R | Napredok Kičevo | - | KF Gostivari | 1:2 (1:0) | ||
| H: 18.09.2013 16:00 | R: 25.09.2013 15:30 | Sieger: Napredok Kičevo | ||||
| H | KF Shkëndija 79 | - | Makedonija GP | 2:0 | ||
| R | Makedonija GP | - | KF Shkëndija 79 | 0:2 | ||
| H: 18.09.2013 16:00 | R: 25.09.2013 16:00 | Sieger: KF Shkëndija 79 | ||||
