It’s May 2021; the National Hockey League playoffs are about to begin. It’s been a season like no other. A global pandemic has kept fans away from arenas in Canada, and the teams, unable to cross the border, have been forced to square off against themselves in an all-Canadian division. It’s been a tough year for everyone – I’m sure the last thing you want is for me to remind you about it. But, in the spring of 2021, there was a light at the end of the tunnel. Restrictions were slowly lifting, fans were gradually being allowed back into their sporting cathedrals, and an old historic rivalry was returning to the playoffs: the Montreal Canadiens vs the Toronto Maple Leafs.
To truly appreciate the occasion of May 2021, we have to understand the history of this rivalry. Toronto and Montreal are separated by 540 killometers, but they’re separated by so much more: culture, language, identity; a history of war, riots, revolution and separatist movements, all boiled together in the modern battlefield of high-level professional sports.
The date is 1760. British forces have marched on Montreal, looking to land a decisive victory against the French in a war between two European superpowers that would decide the fate of Canada forever. The British, 18,000 troops strong, forced the French defenders of Montreal to surrender after a two-month siege. The victorious British were now the masters of Canada and administered control of the French-speaking peoples of Quebec.
As time went on, the settlers in Quebec refused to be culturally assimilated by the British, holding onto their French language and identity. Even at the time of Confederation, nearly 100 years later, the people of Quebec and Montreal remained firmly French.
Toronto, meanwhile, was and remains the largest English-speaking city in Canada. It began with a humble beginning as a town called York on lake Ontario. In the war of 1812, the Americans won the battle of York and preceded to sack the town angering the British and Canadian settlers of the time. York was soon once again in Canadian hands and would never again be threatened. The sacking of york and the immediate turmoil brought with it helped to fuel the flames of nationhood, the people of York slowly began to start to see themselves as Canadians and not just British.
York was later named Toronto, a name that could stand tall amongst the many other settlements called York and despite some setbacks, such as two devastating fires in just over 50 years, the city remained tall as English-speaking Canada’s largest city. As Canada continued to grow and expand in the nation’s early years, both cities became the economic powerhouses of Canada. Being the clear number one and number two most populated cities in Canada and have retained those positions to this day.
In the world of sport, both teams were pioneers in professional hockey. In Toronto after the short-lived existence of the Blueshirts, the franchise that would become known as the Toronto Maple Leafs would join the NHL in 1917. They were to be greeted by a francophone team from Montreal, le Club de hockey Canadien, otherwise known as the Montreal Canadiens, and commonly referred to as the Habs.
The rivalry got off to somewhat of a slow start, with the two teams meeting only twice in the playoffs between 1917 and 1944. That was all about to change however, Toronto and Montreal would run the playoff gauntlet against each other 11 times in 23 years. The two teams quickly became ambassadors for two contracting Canadian societies. Toronto represented an anglophone, protestant Canada on the ice, while Montreal was the champion of the more catholic french-speaking Québécois.
Perhaps the most notable flashpoint of this bad feeling came in March 1955, Maurice Richard, the Canadiens star forward who to many was the embodiment of French Canadian identity on the ice was suspended by the NHL anglophone president Clarence Campbell for the rest of the season including playoffs after a violent altercation with a linesman.

To many Torontonians and English-speaking Canadians, this punishment was too soft, however, in Montreal, the suspension of their hero by an anglophone president of an anglophone league was a move they saw as a direct attack on their culture. Many of Quebec’s industries were controlled by an anglophone elite and French Canadians earned far less than their Anglophone counterparts in the province, there was an ill feeling of Francophones being seen as second class citizens and the Richard lead Canadiens were the pride of French Canada when they won, it was as if they as a people won.
Richard being suspended was more than just a disciplinary preceding, it was an attack on all of Montreal and French Canada. The Richard suspension was the catalyst for riots in the streets of Montreal, a riot that arguably was to become the genesis of a new wave of Québec nationalism and at the time highlighted the ever-growing divide between the people of Toronto and Montreal.

Entering the 1960’s, the rivalry showed no signs of slowing down on or off the ice. Both cities strived to be the powerhouse of Canada. Montreal was awarded the world expo in 1967, Canada’s centennial year and later became the first Canadian city to be awarded an MLB baseball team with the Montreal Expos playing their first season in 1969. Montreal looked to be winning the culture and economic war at the time, the Canadian flag that has dawned a union jack ensign was to be replaced with the iconic Maple leaf flag we know today, much to the distress of many in English speaking Canada and joy of the Québécois.
To this day, the union jack is still part of the flag of Ontario, flying high in buildings in Toronto. Montreal had a larger population than Toronto, the Canadiens had more Stanley Cups and the people of Quebec were becoming more vocal in their French identity, paving the way for much social change in the province.
Toronto loved nothing more at this time to get one over Montreal in the rink, with Montreal hosting the world exhibition, 1967 would prove to be the sweetest victory for Toronto. In Canada’s centennial, the Stanley Cup would return to Toronto with a 4-2 series win over none other than the Canadiens in the final.

As the NHL dawned into a new era of expansion, so would the nature of the Toronto and Montreals rivalry. In the 1970’s Toronto also got a baseball team, adding a new flavour to the rivalry as the Toronto Blue Jays and Montreal Expos competed in the Pearson cup every year from 1977 to 1986. The CN Tower was also completed, an iconic building in Toronto demonstrating the significance the city would have on the world stage as Toronto would go on to surpass and still be the more populated of the two cities.
It was also a very significant decade for Montreal, who in 1976, had the honour of so far being the only Canadian city to host a summer Olympics. But perhaps much more significant, after centuries in the making, French was finally recognized as the official language of Quebec, a landmark moment in the history of the province. With both cities and people of Canada seemingly content, Toronto and Montreal’s on the ice rivalry was cooling down with the two teams meeting only twice in the playoffs, both times being victories for Montreal on their way to further cup glory.
With the two teams being placed in separate conferences in the league, the rivalry and ill-feeling was once again left to politics, as twice in 1980 and 1995 Quebec held referendums on the issue of Quebec sovereignty with the result in 1995 being particularly close. With the two teams being reunited in the same division in 1998, and with the Blue Jays and Expos beginning inter-league play bringing the two cities head to head in the MLB season for the first time, the rivalry would once again be defined through sport.

As the years went by, the two cities would continue to strut their success. Montreal can boast more Stanley cups than Toronto since 1967, with the Leafs owning the unfortunate honour of the league’s longest-ever Stanley cup drought. But Toronto however can boast itself as being arguably a more attractive city for sport. Canadas only current basketball team, the Raptors play in Toronto, and the Blue Jays enjoyed great success in the early ’90s winning two World Series, something the Montreal Expos couldn’t accomplish before the team was forced to relocate to Washington D.C. Despite the introduction of regular matchups with the Jays, Montreal’s financial woes in MLB became overwhelming as the franchise was left with no choice but to start over in D.C.
While the Expos and Blue Jays rivalry never reached the intensity of the Leafs and Habs, the untimely relocation meant there was now an opportunity for the rivalry to open on new frontiers.
Since 1946, Toronto and Montreal have both competed for the Grey Cup and were founding members of the Canadian Football League. Supremacy switched back and forth. The Montreal Alouettes were the team of the ’70s winning three Grey cups which included two playoff wins against the Toronto Argonauts. The tables turned dramatically in the ’80s as Toronto would win a Grey cup in 1983. Meanwhile, the Alouettes would fold in 1982 with the short-lived Concorde’s taking their place before succumbing to the same fate in 1986.
In 1996, the Als were revived and the rivalry in the CFL was truly ignited. From 1996 to 2012, the two rivals locked horns in the playoffs 10 times. These games would be unpredictable with four wins for Toronto and Montreal six times.
Montreal’s Olympic stadium was used for playoff games until 2014, and it wasn’t uncommon to have massive crowds of 60,000 fans turn out to watch these two teams square off for East Division supremacy, whilst in Toronto, 45,000 people were there at the Skydome for playoff match between the two in 2005.
Games between these two would often decide the Grey cup at this time as the two team’s enjoyed unrivalled success in the East Division at this time accounting for all seven Grey cups won by the East division from 1996 to 2012, Toronto having the upper hand with four cups and adding further success in 2017. After 2012, playoff success for both franchises began to wain with the sides not meeting since the 2012 East Final.

Fast forward to the present day of 2021, an upturn in both franchises promises what will surely be more playoff excitement between these two rivals in the very near future.
The Montreal Toronto rivalry was given a new layer in the form of soccer. While soccer clubs in the two cities had existed before, the rivalry really starts in 2008. Montreal was more established, their team, Montreal Impact was a powerhouse in the USL and won the Voyagers cup seven times in a row, cementing themselves as the dominant force in Canadian soccer. The last of those victories came in 2008, where the Voyagers cup was reformatted as the Canadian Championship. They beat out a new MLS expansion team, Toronto FC. Despite Toronto being in a division above, Montreal was still the king of Canada soccer.

S. 2 Ep. 17 – Can Canada Hold Herdman – FC13 Podcast
Then, a year later the rivalry was taken up several notches. In the final game of the 2009 Canadian Championship, Toronto went a goal down away to Montreal and needed to score five unanswered goals to win the championship. Speared on by a hat trick from Canadian soccer legend Dwayne De Rosario, Toronto pulled off what would be dubbed the Miracle in Montreal winning 6-1. Toronto now had a soccer team that could face up to Montreal, opening up yet another front for the eternal rivals.
Montreal joined the MLS in 2012 and it didn’t take long for the rivalry to heat up even more, Montreal defeated Toronto 6-0 in 2013 to avenge the Montreal miracle, and in 2015 they went one better by eliminating Toronto the MLS playoffs. The rivalry reached a zenith in 2016 when the two clubs met in the MLS Eastern Conference final, the most important game involving both cities in a major pan North American sports league since 1979. 61,000 fans attended the first leg at Montreal’s Olympic Stadium, with decibel levels peaking well over 100.

Montreal drew first blood in that game, winning 3-2, but Toronto would secure a famous 7-5 aggregate victory thanks to a 5-2 win in Toronto. Toronto would go all the way the following year winning the MLS cup in 2017 in front of a jubilant home crowd at BMO Field, a landmark achievement for Canadian soccer. Toronto and Montreal haven’t met in the MLS playoffs since, but have continued to dominate the Canadian championship. Toronto and Montreal have won the Canadian championship in each of all but one season, and while Montreal may have changed their name to CF Montreal, the desire for supremely in Canadian soccer is not calming down.
So that brings us back to today, by the end of the 2010s both cities were well established in what they wanted to be and represent. Montreal today is the largest French-speaking city in the developed world outside of Paris. From restaurants menus to tannoy announcements at CF Montreal and Canadiens home games, everything is French first and English last. Much of the city itself has the ethos and architecture more associated with Europe than North America. Montreal is a city that is proud of its French culture and isn’t afraid to let you know it. Montreal is the home of Cirque du Soleil, a reputation for nightlife to rival any city on the continent and the largest international comedy festival in the world, its no wonder it’s been referred to as Canada’s cultural capital.
Toronto meanwhile as a city is Canada’s economic juggernaut, home of financial mammoth the Toronto stock exchange and base of multiple multi-million dollar companies Canadian headquarters, Toronto is the place to be for over six million people. Many people in Canada will mockingly tell you Toronto is the centre of the universe, but you don’t get that title without ambition. Culturally Toronto has an impact well beyond its borders, how many times have a band you liked promised a North American tour, only for Toronto to be the only Canadian city they perform at? How many of you who live outside of Ontario support or know someone who supports the Raptors and Bluejays? Toronto and Montreal embrace being different from each other, they always have been and they always will be.
So here we are, it’s 2021 and Toronto and Montreal are once again fighting for Canadian supremacy as the Maple Leafs and Canadiens faced off in the playoffs for the first time since 1979. Its been a long time since the two teams that catapulted this rivalry into Canadian sporting consciousness have met here, and perhaps it’s only fitting that as life slowly began to return to normal in Toronto and Montreal as the pandemic took its toll, we got to sit down to the most historic and storied rivalry in Canada, and I’m sure I speak for everyone, Anglophone or Francophone when I say I hope this rivalry continues to excite us for years to come on the ice and pitch.
👍 A nice article, trhanks!