Maple Leafs and Canadiens Rivalry: History and Culture

According to our Stanley Cup futures odds here at Ozoon, the Montreal Canadiens are +2200 outsiders to win the title in 2026-27, while the Toronto Maple Leafs are a bit further back at +4000. These numbers will change as roster moves, injuries and game results reshape the betting market; when all is said and done, hese two clubs will have added yet another chapter to the Maple Leafs and Canadiens rivalry, the longest-running in NHL history.

It’s been well over a century since these two iconic teams first met. The Canadiens were officially founded in 1909, making their debut in the old National Hockey Association; the Maple Leafs were born in 1917 when the NHA dissolved and re-emerged as the National Hockey League. That makes the Habs and Leafs the two oldest teams in the NHL.

They were also the NHL’s only Canadian teams following the demise of the Montreal Maroons in 1938. That’s when this rivalry really started to heat up – the Leafs representing the Anglophone side of Canada’s “two solitudes,” and the Habs the Francophone side. Our country’s historic divide between the largely Protestant descendants of the United Empire Loyalists and the Catholic Patriotes provided the fuel for this rivalry; these two teams would go on to win the Stanley Cup in 19 of the NHL’s 25 Original Six seasons. Tensions eased somewhat in 1970 with the arrival of the Vancouver Canucks, along with migration and shifting demographics – you’ll even find Habs fans in Toronto now. But this rivalry is still the biggest thing in hockey, and judging by Ozoon’s Stanley Cup odds, 2026-27 could make it even bigger.

Evolution of the Leafs and Canadiens Rivalry and Key Competitive Moments

The Maple Leafs-Canadiens rivalry wasn’t born out of whole cloth – it took decades to form, layer by layer. Economics laid the groundwork, then league politics gave it shape; the teams and their fans took it from there, one playoff battle after another.

Economic and Cultural Rivalry

Well before the birth of professional sports, or even Canada itself, Montreal and Toronto were competing for commercial supremacy in British North America. Montreal was this nation’s largest city from its incorporation in 1832 until the early 1970s, when the growing financial sector and “Anglo flight” brought much of that business to Toronto. By the mid-20th Century, the economic battle between Montreal and Toronto had become a culture war. Montreal had Expo 67 and the 1976 Summer Olympics; Toronto had the Canadian National Exhibition (CNE) and the explosive growth of their arts/media sector, which allowed “The Big Smoke” to take the lead while Montreal repaid its $1.5-billion Olympic debt.

NHL Origins and Playoff Showdowns

As big as this rivalry has gotten, it wouldn’t be here in the first place without the intransigence of one man: Eddie Livingstone. The owner of the Toronto Blueshirts was so disliked by the other NHA owners, they voted in 1917 to suspend his franchise – then they folded the entire league and re-formed as the NHL.

The league at this point had just four active members: the Canadiens, the Montreal Wanderers, the Ottawa Senators, and the new Toronto Hockey Club, which would later be called the Arenas (after their owners, the Arena Gardens company). The Toronto franchise was then purchased in 1919 by the owners of the St. Patricks Hockey Club, who changed the team name to the Toronto St. Patricks. Conn Smythe eventually took control of the struggling club in 1927, and the Maple Leafs as we know them were born.

When it comes to the playoffs, Toronto only faced the Canadiens a handful of times in those early years. Back when the NHL championship was decided in a two-game, total-goal series (much like soccer and other sports), Toronto won the inaugural title 10-7, while the Habs took the 1924-25 title by a final aggregate score of 5-2. Neither of these series was for the Stanley Cup; Toronto beat the PCHA’s Vancouver Millionaires in 1918, while the WCHL’s Victoria Cougars beat the Habs in 1925, making Victoria the last non-NHL team to win the Cup.

Then came the Original Six Era. After the demise of the Senators in 1935 (following one last-gasp season as the St. Louis Eagles), the Maroons in 1938 and the Brooklyn Americans (formerly the New York Americans) in 1942, the NHL was left with six teams – and that’s how it would stay until the 1967 expansion. This is when the Leafs vs. Habs rivalry took off. They met 11 times in the playoffs; Toronto dominated the postwar period, but Smythe’s right-hand man, Frank J. Selke, moved to Montreal in 1946 and helped pave the way for their later success. Selke’s acrimonious departure also added more fuel to the fire. The tension between the Leafs and Habs was palpable, reaching its peak in 1967 – Canada’s centennial year – when Toronto pulled off the upset and beat Montreal for the Cup in the middle of their Expo 67 glory.

Notable Playoff Series and Results

As you probably know, the Maple Leafs haven’t won the Stanley Cup since. Between expansion and the 1972 ascension of Harold Ballard as majority owner, Toronto’s fortunes changed dramatically – and so have Montreal’s, thanks in large part to the 2004-05 lockout and the arrival of the salary cap. However, the pages of Maple Leafs-Canadiens playoff history continue to be written. Here’s a quick look at their encounters over the years:

– 1918 Toronto won 10-7 (total-goals format)

– 1925 Montreal won 5-2 (total-goals format)

– 1944 Semifinals: Montreal won 4-1 (best-of-seven)

– 1945 Semifinals: Toronto won 4-2

– 1947 Stanley Cup Final: Toronto won 4-2

– 1951 Stanley Cup Final: Toronto won 4-1

– 1959 Stanley Cup Final: Montreal won 4-1

– 1960 Stanley Cup Final: Montreal won 4-0

– 1963 Semifinals: Toronto won 4-1

– 1964 Semifinals: Toronto won 4-3

– 1965 Semifinals: Montreal won 4-2

– 1966 Semifinals: Montreal won 4-0

– 1967 Stanley Cup Final: Toronto won 4-2

– 1978 Semifinals: Montreal won 4-0

– 1979 Quarterfinals: Montreal won 4-0

– 2021 First Round: Montreal won 4-3

Cultural Impact of the Rivalry in Canada

In the modern NHL, “oldest rivalry” doesn’t have the same ring it used to, but this is about more than hockey – it’s our national heritage. The Roch Carrier short story “The Hockey Sweater” (originally published in 1979 as Une abominable feuille d’erable sur la glace) is one of the most revered pieces of Canadian literature, telling Carrier’s real-life childhood tale of how he was forced to wear the Maple Leaf instead of the CH after an Eaton’s order went awry. In 1980, the National Film Board adapted Carrier’s story as an animated short film, narrated by Carrier himself, and an illustrated children’s book was published by Tundra Books in 1984, both to great success.

Habs vs. Leafs has even been built into our infrastructure. Toronto’s College subway station – the stop nearest Maple Leaf Gardens – features a pair of murals called “Hockey Knights in Canada,” depicting the two sides facing off. Commuters pass between the opposing teams every day, paying homage to a rivalry that will continue to extend far beyond the scoreboard.