1st(1st leg) FK Grbalj Radanovići - Iskra Danilovgrad 3:1
2nd (2nd leg) Iskra Danilovgrad - FK Grbalj Radanovići 4:1
1st(1st leg): 02/10/2019 13:30 2nd (2nd leg): 23/10/2019 12:30 Winner: Iskra Danilovgrad
1st(1st leg) FK Ibar Rožaje - FK Zeta 0:0
2nd (2nd leg) FK Zeta - FK Ibar Rožaje 3:0
1st(1st leg): 02/10/2019 13:30 2nd (2nd leg): 23/10/2019 12:30 Winner: FK Zeta
1st(1st leg) FK Sutjeska - FK Lovćen 4:0
2nd (2nd leg) FK Lovćen - FK Sutjeska 0:3
1st(1st leg): 02/10/2019 13:30 2nd (2nd leg): 23/10/2019 12:30 Winner: FK Sutjeska
1st(1st leg) FK Petnjica - FK Podgorica 0:3 dec.
2nd (2nd leg) FK Podgorica - FK Petnjica 3:0 dec.
1st(1st leg): 02/10/2019 13:30 2nd (2nd leg): 23/10/2019 Winner: FK Podgorica
1st(1st leg) FK Rudar Pljevlja - FK Budućnost Podgorica 0:0
2nd (2nd leg) FK Budućnost Podgorica - FK Rudar Pljevlja 2:1
1st(1st leg): 02/10/2019 13:30 2nd (2nd leg): 23/10/2019 12:30 Winner: FK Budućnost Podgorica
1st(1st leg) OFK Petrovac - FK Drezga 2:0
2nd (2nd leg) FK Drezga - OFK Petrovac 9:10 (1:0, 2:0, 2:0) pso
1st(1st leg): 02/10/2019 13:30 2nd (2nd leg): 23/10/2019 12:30 Winner: OFK Petrovac
1st(1st leg) FK Bokelj - OFK Titograd 1:2
2nd (2nd leg) OFK Titograd - FK Bokelj 2:1
1st(1st leg): 02/10/2019 13:30 2nd (2nd leg): 23/10/2019 12:30 Winner: OFK Titograd