Period 2006-2016
First winner of competition was FK Rudar, who won the title on season 2006–07 without any defeat in eight matches. In the final game, FK Rudar defeated FK Sutjeska - 2-1. That was the first official trophy won in Montenegrin football since independence. On previous phases, FK Rudar eliminated FK Mornar (1-0), FK Berane (1-1, 2-0), OFK Titograd (2-0, 0-0) and OFK Grbalj (0-0, 2-0). Notable games also came in Round of 16, with matches between two strongest sides during that season - FK Budućnost and FK Zeta. First game, attended by 10,000 spectators, won FK Budućnost (2-0), but FK Zeta made biggest win in second game in Golubovci (3-0).
Next season, trophy won FK Mogren, who won the final match against FK Budućnost on penalties (1-1; 6-5). Game for trophy was attended by 10,000 spectators and that was the highest audience on Montenegrin Cup finals. Previously, FK Mogren eliminated FK Pljevlja (5-0), FK Sutjeska (1-1, 1-0), OFK Petrovac (0-0, 1-0) and title-holder side FK Rudar (1-0, 0-0). During that season, FK Berane became first Second League side to reach the semifinals of Montenegrin Cup.
On season 2008–09, the trophy won OFK Petrovac, defeating Lovćen in extra-time (0-0; 1-0). Meeting of two teams in final was surprise, as they in semifinals eliminated strongest teams as FK Budućnost and FK Rudar. During the season, before the final, OFK Petrovac previously eliminated FK Pljevlja (1-0), FK Otrant (2-0, 3-0), FK Mogren (1-0, 2-1) and FK Rudar (0-0, 0-0; penalties: 5-3).
FK Rudar was the first, and until now the only club which won two trophies in a row. They won the title on season 2009–10 with win against FK Budućnost in final (2-1). During that Cup campaign, team from Pljevlja previously eliminated FK Sloga Bar (7-0), FK Jedinstvo (1-1, 2-0), FK Mornar (6-1, 0-0) and OFK Petrovac (2-1, 0-0)
Next year, FK Rudar defended the title after penalties in the final game against FK Mogren. After the 90 minutes, game finished with result 2-2, which was the biggest number of goals in the final until then. That was the third title for FK Rudar since establishing of Montenegrin Cup. Except they defended the trophy, coach of FK Rudar Nebojša Vignjević became the first manager who won two editions of Montenegrin Cup. Before the final, FK Rudar eliminated FK Crvena Stijena (2-0, 2-1), FK Sutjeska (0-0, 2-1) and FK Zeta (1-0, 2-2).
Season 2011–12 is remembered by the fact that one team from Montenegrin Second League won the Cup trophy. Big surprise made FK Čelik from Nikšić, who defeated Rudar in the final match - 2:1. That was the first defeat of FK Rudar in Montenegrin Cup after the season 2008-09 and 28 consecutive wins and draws. After the victory in the Cup finals, FK Čelik became first Second League side who gained participation in European competitions. Except that, striker Veselin Bojić became the first player who scored two goals in two different Montenegrin Cup finals for two different teams (2010-11 for FK Rudar; 2011-12 for FK Čelik). In previous rounds, team from Nikšić eliminated FK Blue Star (2-0), FK Lovćen (1-0, 1-0), FK Bokelj (1-1, 1-0) and FK Jedinstvo (3-0, 0-1).
Year later, FK Čelik again played in the finals, but as a member of Montenegrin First League. Team from Nikšić was defeated by FK Budućnost (1:0), who held the first trophy after their third performance in final. The only goal was scored in additional time, by FK Budućnost striker Mitar Peković. In previous games, FK Budućnost eliminated FK Bratstvo (3-0), FK Jedinstvo (2-0, 1-0), FK Zeta (2-0, 2-0) and OFK Titograd (3-2, 1-1). During the first leg of competition, OFK Titograd defeated FK Pljevlja 10-1 and that's among the highest home wins in the history of Montenegrin Cup. During the same game, striker Luka Rotković scored seven goals, which is another all-time record of competition.
On season 2013–14, Lovćen won the trophy for the first time in the club's history. Team from Cetinje won the final game against OFK Titograd - 1-0. Before the final match, FK Lovćen eliminated FK Zora (1-0), FK Crvena Stijena (8-0, 1-2), FK Zeta (1-0, 1-2) and OFK Petrovac (3-0, 0-0).
OFK Titograd succeeded to hold the trophy for season 2014–15. In the finals, they defeated OFK Petrovac in extra-time (2-1). In previous rounds, OFK Titograd defeated FK Mogren (1-2, 5-1), FK Zeta (0-0, 0-0; penalties: 4-3) and FK Sutjeska (2-0, 2-0). During the same season, in first leg, FK Budućnost defeated FK Pljevlja 9-0, which is another game among the highest home wins in history of Montenegrin Cup.
Rudar won their fourth Cup trophy on season 2015–16. In final match, team from Pljevlja won the penalties against Budućnost (4-3) after the goalless 120 minutes. With that game, FK Rudar became the first team to participate in five Montenegrin Cup finals. Before the game for trophy, they eliminated FK Radnički (1-0), FK Sutjeska (1-0, 3-0), FK Dečić (2-1, 2-2) and FK Bokelj (2-0, 1-0).
Period 2016-
For the first time in their history, FK Sutjeska became a title-holder on season 2016–17, winning the finals against Grbalj (1-0). That was the second performance of FK Sutjeska in Montenegrin Cup final. In previous rounds, they defeated FK Radnički (5-0), FK Zeta (2-2, 1-0), OFK Petrovac (1-0, 1-2) and FK Iskra (4-3, 5-0).
In 2017–18 Montenegrin Cup, for the second time in history, one team from Second League participated in the finals. That was FK Igalo, which played against OFK Titograd who won the game with 2-0. That was the second trophy for OFK Titograd. On that game, striker Admir Adrović became the first player who scored twice on one final match. Except that, coach Aleksandar Miljenović became the first manager who won two Cup trophies with two different clubs (2008-09 with OFK Petrovac, 2017-18 with OFK Titograd). On their road to final, OFK Titograd eliminated FK Čelik (9-1), FK Zeta (4-0, 2-1), FK Mornar (3-0, 2-0) and FK Budućnost (1-2, 2-1; penalties: 4-3).
Season 2018-19 finished with the second title won by FK Budućnost. Team from Podgorica in the finals won against FK Lovćen - 4:0. That was the biggest win in the history of Montenegrin Cup finals. Except that, FK Budućnost player Mihailo Perović scored a first ever hattrick [4] in the finals. Before the game for trophy, FK Budućnost eliminated FK Rudar (1-0, 0-0), FK Podgorica (1-1, 1-0) and, in the semifinals, FK Sutjeska (0-0, 1-1).
On season 2019-20, Montenegrin Cup was interrupted in March 2020, before the semifinals, due to the coronavirus pandemic. Semifinalists were FK Budućnost, FK Sutjeska, FK Podgorica and OFK Petrovac. Three months after that, Football Association of Montenegro decided that Montenegrin Cup for the season 2019-20 won't be continued. [5]
Due to pandemic, edition 2020-21 was played with different format. Only 16 teams participated and, until the semifinals, in previous rounds teams played only one game. At the end, Football Association of Montenegro decided that the finals will be played in front of limited audience on Podgorica City Stadium. That was the first football match in Montenegro with spectators after nearly 15 months of COVID-19 pandemic. Once again, the Cup won FK Budućnost, which defeated Dečić in the finals (3-1). That was first 'double' for FK Budućnost, who previously won fifth title in Montenegrin First League, but the second 'double' in the history of Montenegrin football, too. For FK Dečić, that was the first participation in Cup finals.
Montenegro 
2023–24 Montenegrin Cup 
