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| U | FK Grbalj Radanovići | - | FK Iskra Danilovgrad | 3:1 | ||
| R | FK Iskra Danilovgrad | - | FK Grbalj Radanovići | 4:1 | ||
| U: 02.10.2019 14:30 | R: 23.10.2019 13:30 | Winnaars: FK Iskra Danilovgrad | ||||
| U | FK Ibar Rožaje | - | FK Zeta | 0:0 | ||
| R | FK Zeta | - | FK Ibar Rožaje | 3:0 | ||
| U: 02.10.2019 14:30 | R: 23.10.2019 13:30 | Winnaars: FK Zeta | ||||
| U | FK Sutjeska | - | FK Lovćen | 4:0 | ||
| R | FK Lovćen | - | FK Sutjeska | 0:3 | ||
| U: 02.10.2019 14:30 | R: 23.10.2019 13:30 | Winnaars: FK Sutjeska | ||||
| U | FK Petnjica | - | FK Podgorica | 0:3 Toeg. | ||
| R | FK Podgorica | - | FK Petnjica | 3:0 Toeg. | ||
| U: 02.10.2019 14:30 | R: 23.10.2019 | Winnaars: FK Podgorica | ||||
| U | FK Rudar Pljevlja | - | FK Budućnost Podgorica | 0:0 | ||
| R | FK Budućnost Podgorica | - | FK Rudar Pljevlja | 2:1 | ||
| U: 02.10.2019 14:30 | R: 23.10.2019 13:30 | Winnaars: FK Budućnost Podgorica | ||||
| U | OFK Petrovac | - | FK Drezga | 2:0 | ||
| R | FK Drezga | - | OFK Petrovac | 9:10 (1:0, 2:0, 2:0) d.p. | ||
| U: 02.10.2019 14:30 | R: 23.10.2019 13:30 | Winnaars: OFK Petrovac | ||||
| U | FK Bokelj | - | OFK Titograd | 1:2 | ||
| R | OFK Titograd | - | FK Bokelj | 2:1 | ||
| U: 02.10.2019 14:30 | R: 23.10.2019 13:30 | Winnaars: OFK Titograd | ||||
