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The Montreal Canadiens and Toronto Maple Leafs are considered to be the oldest rivalry in the NHL.
Since the NHL added a franchise in Toronto in 1917.
The Canadiens and the Maple Leafs met in the postseason for the first time at the end of the inaugural NHL season, but back then, the Leafs they were called the Blueshirts because they had no official name yet.
The Canadiens and Maple Leafs have met in the playoffs 15 times. To date, Montreal has won 8, Toronto 7. Scores of games won by the series winning team are in bold.
Notably, the Canadiens and the Maple Leafs have won the most Stanley Cups in the NHL, with 24 and 13, respectively. As a result of their success, they have the two largest fanbases in the entire league – both teams have an influx of visiting fans in their home arenas when they play each other.