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| 1st(1st leg) | FK Bregalnica Štip | - | KF Shkëndija 79 | 2:1 | ||
| 2nd (2nd leg) | KF Shkëndija 79 | - | FK Bregalnica Štip | 1:1 | ||
| 1st(1st leg): 12/10/2013 13:00 | 2nd (2nd leg): 20/11/2013 12:00 | Winner: FK Bregalnica Štip | ||||
| 1st(1st leg) | FK Pelister | - | FK Rabotnički | 1:0 | ||
| 2nd (2nd leg) | FK Rabotnički | - | FK Pelister | 2:0 | ||
| 1st(1st leg): 13/10/2013 13:00 | 2nd (2nd leg): 04/12/2013 12:00 | Winner: FK Rabotnički | ||||
| 1st(1st leg) | FK Teteks | - | Napredok Kičevo | 0:0 | ||
| 2nd (2nd leg) | Napredok Kičevo | - | FK Teteks | 1:2 | ||
| 1st(1st leg): 13/10/2013 13:00 | 2nd (2nd leg): 20/11/2013 12:00 | Winner: FK Teteks | ||||
| 1st(1st leg) | FK Drita | - | Metalurg Skopje | 0:3 | ||
| 2nd (2nd leg) | Metalurg Skopje | - | FK Drita | 7:1 | ||
| 1st(1st leg): 13/10/2013 13:00 | 2nd (2nd leg): 20/11/2013 12:00 | Winner: Metalurg Skopje | ||||
