Canadian Classique

The first professional soccer clubs to be played in either Toronto or Montreal were the Toronto Metros and Montreal Olympique, who both began play in 1971. The two teams played infrequently due to consistent relocation and expansion/contraction in the old North American Soccer League. Throughout the 1980s, different teams from both respective metropolises formed and folded, rarely aligned with one another at the same season.

In 1992, the original Montreal Impact side formed by the Saputo family, following the demise of Montreal Supra and its league (the Canadian Soccer League). They became a dominant club in the American Professional Soccer League (1993–1996) and the A-League (1997–2003), renamed the USL First Division (2004). The team did not compete during the 1999 A-League season. Their main rivals were the Rochester Rhinos and the Toronto Lynx prior to the latter's move to the USL Premier Development League.

The modern day rivalry involving Toronto FC came into fruition during the first ever Canadian Championship, Canada's domestic cup competition that was formed in 2008. The tournament is used as well to determine Canada's sole berth into the CONCACAF Champions League. It was the 2008 edition of the tournament where Montreal and Toronto played their first competitive game against one another. Played on May 27, 2008, Toronto emerged victorious 1–0 over thanks to a Marco Vélez goal in the 72nd minute in front of a crowd of 12,303 at Saputo Stadium.[12] Toronto, being the lone MLS team in the tournament, despite being an expansion franchise, was expected to ultimately win the tournament. Ultimately, though, the Impact ended up winning the three-way tournament, against Toronto and Vancouver Whitecaps, achieving the first Canadian Championship after posting a 2–1–1 record. The title was clinched by Montreal against Toronto on Toronto's home ground, BMO Field. The 1–1 draw which gave Montreal the title on Toronto's home soil further fueled the rivalry. By winning that title, Montreal earned a berth into the 2008–09 CONCACAF Champions League where they reached the quarterfinals.

Toronto got revenge on the Montreal at the following Canadian Championship by scoring six unanswered goals in a come-from-behind 6–1 win at Saputo Stadium. Toronto captain, Dwayne De Rosario netted a hat trick in the match. The match also secured Toronto's place in the 2009–10 CONCACAF Champions League, where they were eliminated in the preliminary round of the tournament. The Reds continued their reign of dominance in the 2010 edition of the Canadian Championship, beating Montreal in both the home and away legs of the competition, tallying an aggregate score of 3–0 during that time. With the arrival of FC Edmonton, the 2011 edition of the competition did not see the Impact and Reds meet each other.

It was around this time that it was announced that the Impact would be "promoted" to Major League Soccer at the start of the 2012. The announcement officially came from MLS commissioner, Don Garber and the Saputo family on May 7, 2010.[13] On June 14, 2011, the Montreal Impact announced a five-year agreement with the Bank of Montreal to become their lead sponsor and jersey sponsor in MLS, the same kit sponsor of Toronto.[14]

Montreal and Toronto played their first MLS competition on April 7, 2012.[15] Played in front of a crowd of 24,000 at Olympic Stadium, the Impact emerged victorious, 2–1, over the Reds. Bosnian Siniša Ubiparipović netted the opening goal of the derby in MLS competitions, scoring for Montreal in the 18th minute. Andrew Wenger, the first pick of the 2012 MLS SuperDraft, netted in the 81st minute to give the Impact the game-winning goal. Dutch international Danny Koevermans netted a consolation goal for Toronto in the 88th minute.

In 2013, the Reds and Impact split the series 1–1–1. A crowd of 38,000 was on hand to watch the first match of the 2013 series, where Montreal won 2–1. Additionally, in 2013, the Impact won their first Canadian Championship since joining MLS. During their 2013 Canadian Championship run, the Impact defeated Toronto by a 6–0 scoreline, to date, the largest margin of victory in the derby history.[16]

On April 24, 2013, Justin Braun became the first player to play for both sides of the derby, after he was traded from Montreal to Toronto over the winter break. Collen Warner repeated the feat in 2014 after being traded to Toronto for Issey Nakajima-Farran, who had never played against Montreal before the exchange. Dominic Oduro (2015) and Kyle Bekker (2016) later joined the turncoat club, both playing for Toronto before Montreal. Canadian goalkeeper Greg Sutton played for both the NASL edition of the Montreal Impact and for Toronto FC, but only ever played for the Reds in derby matches. No player has ever scored a goal for both teams in derby matches.

October 29, 2015 was the first time that the teams met in the MLS Cup Playoffs. The match at Saputo Stadium ended 3–0 in favour of the Impact.[17] It also marked Toronto's first appearance in the playoffs in their history,[18] and Montreal's second-ever playoff game. The two teams faced off again for the second consecutive time in the 2016 MLS Cup Playoffs in two games as both Toronto and Montreal defeated New York City FC and New York Red Bulls respectively, making the rivalry part of the Eastern Conference Finals. Montreal won the first leg of the Conference Championship, 3–2 at the Olympic Stadium in Montreal on November 22. Toronto later beat Montreal 5–2 in extra time in the return leg at BMO Field in Toronto on November 30, winning on an aggregated score of 7–5, making Toronto FC the first Canadian team to compete in an MLS Cup Final.[19]

As of September 9, 2020

Jozy Altidore's dozen goals for Toronto FC make him the series' top goalscorer

Pos	Name	Club	Nationality	Goals
1	Jozy Altidore	Toronto FC	United States	12
2	Ignacio Piatti	Montreal Impact	Argentina	11
3	Sebastian Giovinco	Toronto FC	Italy	10
4	Dominic Oduro	Montreal Impact	Ghana	5
		Toronto FC
5	Dwayne De Rosario	Toronto FC	Canada	4
	Marco Di Vaio	Montreal Impact	Italy
	Didier Drogba	Montreal Impact	Ivory Coast
	Tosaint Ricketts	Toronto FC	Canada
9	Ayo Akinola	Toronto FC	United States	3
	Chad Barrett	Toronto FC	United States
	Jordan Hamilton	Toronto FC	Canada
12	15 players			2

Players in bold are still active players with the team.

• Kyle Bekker
• Raheem Edwards
• Daniel Lovitz
• Issey Nakajima-Farran
• Dominic Oduro
• Maxi Urruti

• Justin Braun
• Adam Braz
• Laurent Ciman
• Ali Gerba
• Greg Sutton
• Collen Warner