1st(1st leg) KF Shkëndija 79 - FK Rabotnički 1:1
2nd (2nd leg) FK Rabotnički - KF Shkëndija 79 2:2 (0:1)
1st(1st leg): 04/12/2019 12:00 2nd (2nd leg): 04/03/2020 13:00 Winner: KF Shkëndija 79
1st(1st leg) KF Shkupi - Akademija Pandev 0:1
2nd (2nd leg) Akademija Pandev - KF Shkupi 1:1 (0:0)
1st(1st leg): 04/12/2019 12:00 2nd (2nd leg): 04/03/2020 13:00 Winner: Akademija Pandev
1st(1st leg) FC Struga - FK Renova 0:0
2nd (2nd leg) FK Renova - FC Struga 1:2 (1:1)
1st(1st leg): 04/12/2019 12:00 2nd (2nd leg): 04/03/2020 13:00 Winner: FC Struga
1st(1st leg) FK Bregalnica Štip - FK Labuništa 1:0
2nd (2nd leg) FK Labuništa - FK Bregalnica Štip 1:4 (0:3)
1st(1st leg): 04/12/2019 15:30 2nd (2nd leg): 04/03/2020 13:00 Winner: FK Bregalnica Štip