1st(1st leg) FK Pelister - Sileks Kratovo 1:0 (0:0)
2nd (2nd leg) Sileks Kratovo - FK Pelister 1:2 (0:1)
1st(1st leg): 23/11/2016 12:30 2nd (2nd leg): 07/12/2016 12:00 Winner: FK Pelister
1st(1st leg) Metalurg Skopje - Vardar Skopje 1:4 (0:4)
2nd (2nd leg) Vardar Skopje - Metalurg Skopje 4:1 (1:0)
1st(1st leg): 23/11/2016 12:30 2nd (2nd leg): 07/12/2016 12:00 Winner: Vardar Skopje
1st(1st leg) KF Shkupi - KF Shkëndija 79 0:0 (0:0)
2nd (2nd leg) KF Shkëndija 79 - KF Shkupi 4:0 (3:0)
1st(1st leg): 23/11/2016 12:30 2nd (2nd leg): 07/12/2016 12:00 Winner: KF Shkëndija 79
1st(1st leg) FK Pobeda Junior - FK Bregalnica Štip 2:2 (1:1)
2nd (2nd leg) FK Bregalnica Štip - FK Pobeda Junior 3:0 (1:0)
1st(1st leg): 23/11/2016 12:30 2nd (2nd leg): 07/12/2016 12:00 Winner: FK Bregalnica Štip