In the intervening years since the club's formation, they had beaten Aberdeen and played several teams from the West of Scotland such as Dumbarton, Third Lanark Volunteers and Glasgow Thistle.

Keillor received one more cap during his time at Montrose, scoring the opening goal in a 3–2 victory over Ireland in Belfast during the 1891–92 British Home Championship.

[4] George Bowman also captained Montrose to their first piece of silverware, the Forfarshire Cup, with a 5–3 win over Dundee East End in the 1892 final at West Craigie Park.

[5] In 1921, Montrose won the Scottish Qualifying Cup after defeating Nithsdale Wanderers 2–1 in the second replay of the final at Ibrox.

However, the following season Montrose finished at the bottom of the table, and despite signs of a recovery in 1925–26, lost their league place when the Third Division was scrapped owing to the financial difficulties experienced by many of the member clubs.

Perhaps the best result of that difficult decade came in the 1938–39 Scottish Cup, when in the first round, Montrose sensationally knocked out holders East Fife by a 2–1 scoreline at Bayview Park.

In the second round of 1974–75 Scottish Cup, Montrose recorded their largest victory in modern times when they beat Vale of Leithen 12–0.

In the 1975–76 Scottish Cup quarter-final, Montrose were only 90 seconds away from a famous victory in front of over 8,000 spectators at Links Park against Hearts, until an injury time equaliser from Graham Shaw sent the match to a replay.

Under co-managers Doug Rougvie and Chic McLelland, Montrose won promotion to Division One in 1991, after finishing as runners-up to Stirling Albion, but were relegated after one further season in the higher league.

Following a disappointing beginning to 2005–06 season, manager Henry Hall left the club by mutual consent, shortly followed by assistant Ian Gilzean.

David Robertson (ex Aberdeen, Rangers and Leeds United player) became co-manager with Wolecki, but the latter parted company with the club in September 2006.

Following a very poor run of results David Robertson left the club in early 2007, replaced in time by ex-St Johnstone stalwart Jim Weir, assisted by experienced defender Kevin McGowne.

The 2008–09 pre-season was very quiet and few new signings were made; rumblings of discontent and rumours of behind the scenes fighting were proved to be true as boss Jim Weir was sacked by the Board after a 2–1 defeat to Cowdenbeath with six months still to run on his contract.

Ray Farningham & Stuart Garden were given the job of leading the team till the end of the season however the board moved quickly to secure the pair on two year contracts.

During the 2012–13 season, Montrose faced Rangers four times in the league due to the latter's financial troubles and subsequent placement into the Scottish Third Division.

Two goals in the second half of the home leg by Marvin Andrews and Gary Wood saved the club from dropping into non-league football.

[8] Stewart Petrie was appointed manager in December 2016 after the sacking of Paul Hegarty a month earlier due to a run of poor performances, which led to the club sitting bottom of League Two.

[9] The appointment of Petrie vastly improved the fortunes of the team, achieving a 4th-place finish at the end of season and qualification for the League One playoffs for the first time in nine years.

After promotion, Petrie continued to steer the club in a favourable direction in League One, achieving top four finishes and Championship playoff spots for four consecutive seasons.

During the 2023–24 season, Montrose had three matches televised live on BBC Alba, including a 3–2 win over Queen of the South at Palmerston Park.