Achtste finale
02.10.2019 14:30 FK Grbalj Radanovići FK Grbalj Radanovići - Iskra Danilovgrad Iskra Danilovgrad 3:1
02.10.2019 14:30 FK Ibar Rožaje FK Ibar Rožaje - FK Zeta FK Zeta 0:0
02.10.2019 14:30 FK Sutjeska FK Sutjeska - FK Lovćen FK Lovćen 4:0
02.10.2019 14:30 FK Petnjica FK Petnjica - FK Podgorica FK Podgorica 0:3 Toeg.
02.10.2019 14:30 FK Rudar Pljevlja FK Rudar Pljevlja - FK Budućnost Podgorica FK Budućnost Podgorica 0:0
02.10.2019 14:30 OFK Petrovac OFK Petrovac - FK Drezga FK Drezga 2:0
02.10.2019 14:30 FK Bokelj FK Bokelj - OFK Titograd OFK Titograd 1:2
23.10.2019 FK Podgorica FK Podgorica - FK Petnjica FK Petnjica 3:0 Toeg.
23.10.2019 13:30 Iskra Danilovgrad Iskra Danilovgrad - FK Grbalj Radanovići FK Grbalj Radanovići 4:1
23.10.2019 13:30 FK Zeta FK Zeta - FK Ibar Rožaje FK Ibar Rožaje 3:0
23.10.2019 13:30 FK Lovćen FK Lovćen - FK Sutjeska FK Sutjeska 0:3
23.10.2019 13:30 FK Budućnost Podgorica FK Budućnost Podgorica - FK Rudar Pljevlja FK Rudar Pljevlja 2:1
23.10.2019 13:30 FK Drezga FK Drezga - OFK Petrovac OFK Petrovac 9:10 (1:0, 2:0, 2:0) d.p.
23.10.2019 13:30 OFK Titograd OFK Titograd - FK Bokelj FK Bokelj 2:1
Kwartfinale
06.11.2019 13:30 Jedinstvo Bijelo Polje Jedinstvo Bijelo Polje - FK Budućnost Podgorica FK Budućnost Podgorica 0:1
27.11.2019 13:00 FK Zeta FK Zeta - FK Sutjeska FK Sutjeska 0:0
27.11.2019 13:00 OFK Titograd OFK Titograd - OFK Petrovac OFK Petrovac 0:0
27.11.2019 16:00 FK Podgorica FK Podgorica - Iskra Danilovgrad Iskra Danilovgrad 0:0
27.11.2019 17:00 FK Budućnost Podgorica FK Budućnost Podgorica - Jedinstvo Bijelo Polje Jedinstvo Bijelo Polje 7:0
15.12.2019 13:00 Iskra Danilovgrad Iskra Danilovgrad - FK Podgorica FK Podgorica 1:1
15.12.2019 13:00 FK Sutjeska FK Sutjeska - FK Zeta FK Zeta 1:0
15.12.2019 13:00 OFK Petrovac OFK Petrovac - OFK Titograd OFK Titograd 2:0
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