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| 1st(1st leg) | Metalurg Skopje | - | Vardar Skopje | 1:0 | ||
| 2nd (2nd leg) | Vardar Skopje | - | Metalurg Skopje | 2:1 (2:1) | ||
| 1st(1st leg): 18/09/2013 15:00 | 2nd (2nd leg): 25/09/2013 14:30 | Winner: Metalurg Skopje | ||||
| 1st(1st leg) | FK Turnovo | - | FK Bregalnica Štip | 1:0 | ||
| 2nd (2nd leg) | FK Bregalnica Štip | - | FK Turnovo | 3:0 pso | ||
| 1st(1st leg): 18/09/2013 15:00 | 2nd (2nd leg): 25/09/2013 15:00 | Winner: FK Bregalnica Štip | ||||
| 1st(1st leg) | FK Teteks | - | FK Renova | 2:2 | ||
| 2nd (2nd leg) | FK Renova | - | FK Teteks | 4:5 pso | ||
| 1st(1st leg): 18/09/2013 15:00 | 2nd (2nd leg): 25/09/2013 15:00 | Winner: FK Teteks | ||||
| 1st(1st leg) | FK Pelister | - | FK Miravci | 2:0 | ||
| 2nd (2nd leg) | FK Miravci | - | FK Pelister | 2:3 pso | ||
| 1st(1st leg): 18/09/2013 15:00 | 2nd (2nd leg): 25/09/2013 15:00 | Winner: FK Pelister | ||||
| 1st(1st leg) | FK Rabotnički | - | FK Novaci 2005 | 4:0 | ||
| 2nd (2nd leg) | FK Novaci 2005 | - | FK Rabotnički | 1:2 (1:1) | ||
| 1st(1st leg): 18/09/2013 15:00 | 2nd (2nd leg): 25/09/2013 14:30 | Winner: FK Rabotnički | ||||
| 1st(1st leg) | Sileks Kratovo | - | FK Drita | 1:0 | ||
| 2nd (2nd leg) | FK Drita | - | Sileks Kratovo | 8:7 (1:0, 1:0) pso | ||
| 1st(1st leg): 18/09/2013 15:00 | 2nd (2nd leg): 25/09/2013 14:30 | Winner: FK Drita | ||||
| 1st(1st leg) | KF Gostivari | - | Napredok Kičevo | 0:3 | ||
| 2nd (2nd leg) | Napredok Kičevo | - | KF Gostivari | 1:2 (1:0) | ||
| 1st(1st leg): 18/09/2013 15:00 | 2nd (2nd leg): 25/09/2013 14:30 | Winner: Napredok Kičevo | ||||
| 1st(1st leg) | KF Shkëndija 79 | - | Makedonija GP | 2:0 | ||
| 2nd (2nd leg) | Makedonija GP | - | KF Shkëndija 79 | 0:2 | ||
| 1st(1st leg): 18/09/2013 15:00 | 2nd (2nd leg): 25/09/2013 15:00 | Winner: KF Shkëndija 79 | ||||
