The Toronto Maple Leafs-Montreal Canadiens rivalry is one the of the oldest and most bitter in North American sports. The rivalry extends to the general competitive nature that exists between the cities of Toronto, Ontario, and Montreal, Quebec. The two Canadian cities, each vast metropolitan areas with millions of residents, have major cultural differences, as well as similarities, that intensifies the rivalry.
From 1923 to 1969, the Maple Leafs and Canadiens met each other in the playoffs 12 times, and faced off in five Stanley Cup Finals. While the on-ice competition is fierce, the Leafs-Canadiens rivalry is actually symbolic of a much deeper cleavage in Canadian history and society. The rivalry is merely a figurehead of the larger rivalry that exists between English and French Canadians. The rivalry is also a rivalry between Canada's largest cities. Toronto, the largest, is the heart of English Canada, while Montreal, the second-largest, is the heart of French Canada.
From the time of the British conquest of Quebec at the Plains of Abraham in 1759, the chief tension in what eventually became Canada has been between English and French speaking Canadians. The American-Canadians were, for the most part, of British ethnic stock and Protestant, and possessed conservative and imperialist loyalties. The French Canadians, meanwhile, were not only of French descent, but were also Roman Catholic in religion, politically liberal, and continentalist in economic thought.
When the NHL was created in 1917, these differences received the opportunity to play themselves out in a rivalry between the antagonists Toronto Maple Leafs and the protagonists Montreal Canadiens. The Maple Leafs' fanbase consisted mainly of English-speaking Canadians of British descent. In fact, the team's logo was, in essence, a stylized version of the Canadian Army's Cap Badge Insignia during World War I. This held particular significance for Leaf owner Conn Smythe, who had served as an artillery officer during the Great War. As late as the 1970s, a portrait of Queen Elizabeth II, Queen of Canada, was hung in the Leafs' home arena, Maple Leaf Gardens, and God Save the Queen was sung as an anthem before the game. The Canadiens, meanwhile, captured the imaginations of French-speaking fans, mainly concentrated in the province of Quebec (and to a slightly lesser degree, English-speaking Catholic and Jewish fans in Montreal, as well as English-speaking Catholic fans in eastern Ontario and the Maritimes). In stark contrast to the anthem practice in Toronto, the Habs pioneered the use of the current Canadian national anthem, "O Canada," at the Montreal Forum.
While certainly heated during the 1940s and 1950s, the Leafs-Habs rivalry was particularly acute during the 1960s, as one of the two teams would capture the Stanley Cup each year in the decade, with the exceptions of 1961 and 1970. The rivalry perhaps reached its zenith in the 1967 season, when both teams met in the Stanley Cup Finals during the centennial year of Canadian Confederation. The city of Montreal was hosting Expo 67 that year, and the Canadiens were expected to beat the Leafs quite handily. Still, underdog Toronto upset the Habs to capture the championship.
After 1967, the rivalry cooled slightly due to NHL expansion and realignment. The fanbases of both teams began to erode somewhat as new franchises in Vancouver, Calgary, Edmonton and Winnipeg captured the allegiances of English-speaking fans in Western Canada, while the Quebec Nordiques competed with the Canadiens for the loyalties of Francophone fans within Quebec from 1979 to 1995. From 1981 to 1998, Toronto and Montreal were in opposite conferences, as the Maple Leafs were in the Clarence Campbell/Western Conference and the Canadiens were in the Prince of Wales/Eastern Conference. The fortunes of the two teams since 1967 have also seen a marked difference as the Habs have won ten Stanley Cup championships since that year, while the Maple Leafs still have yet to reach the Stanley Cup Finals. Toronto came close to reaching the Finals in 1993, where they would have faced the Wales Conference champion Canadiens in the 100th anniversary year of the Stanley Cup. However, they were narrowly defeated in the Campbell Conference Finals by the Los Angeles Kings which the Canadiens eventually won the cup. This rivalry is featured in the murals of Toronto's College subway station.
In 1998, the Leafs moved into the Eastern Conference's Northeast Division, along with the Canadiens, Ottawa Senators, Buffalo Sabres, and Boston Bruins. This has served to rekindle the rivalry somewhat, although the two teams have yet to appear in a playoff series against each other like 2018 playoffs where the Habs swept the Leafs in pieces.