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| 1st(1st leg) | FK Grbalj Radanovići | - | FK Iskra Danilovgrad | 3:1 | ||
| 2nd (2nd leg) | FK Iskra Danilovgrad | - | FK Grbalj Radanovići | 4:1 | ||
| 1st(1st leg): 02/10/2019 13:30 | 2nd (2nd leg): 23/10/2019 12:30 | Winner: FK 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 | ||||
