Montreal Canadiens Playoff History (1909-2026)

The Montreal Canadiens are the winningest NHL franchise by a considerable margin, with 24 Stanley Cups and many close calls. 

Their history is replete with unforgettable moments, and the franchise enjoyed three distinct dynasties, cleaning up with a collection of Cups that would be impossible to repeat today. 

If the BetMGM sportsbook were around during those dynasties, the Canadiens would have consistently been the Stanley Cup odds favourites.

NHL Playoffs: Canadiens History 

The Canadiens know a thing or two about playoff hockey. Since the NHL’s inaugural season in 1917, the Canadiens have only missed the playoffs 21 times. 

That’s 88 playoff appearances. While it helped that only two of six teams didn’t make the playoffs until the NHL expanded to 12 teams in 1967, it’s still an incredible success story. 

Their longest streak without a playoff appearance is three seasons, which has occurred three times, the most recent being from 2022 to 2024. 

Canadiens Stanley Cups

Of their 24 Cups, 14 came before the NHL expanded to 12 teams in 1967. The franchise has beaten the Boston Bruins seven times in the Stanley Cup Final, more than any other team. 

Their three dynasties occurred over three distinct periods: The first saw the Canadiens advance to 10 straight Stanley Cup Finals between 1951 and 1960. They won six championships in eight years from 1953 to 1960, including a run of five successive Cups between 1956 and 1960. 

While the run from 1956 to 1960 was the only time the Canadiens won five in a row, they captured four straight from 1965 to 1969, making five successive finals. That constituted the franchise’s second dynasty. 

Their final dynasty occurred from 1976 to 1979, when they won four consecutive Stanley Cups for the third time.

Since the NHL’s first season in 1917, the Habs have played in 35 Stanley Cup Finals, losing 11. Their last defeat in a Stanley Cup Final occurred in 2021 to the Tampa Bay Lightning. 

How Many Stanley Cups Have the Canadiens Won? 

The Canadiens have won 24 Stanley Cups, the most of any team. The Toronto Maple Leafs are in a distant second with 13 Cups. 

How Many Stanley Cups Have the Canadiens Won Since the Best-of-7 Introduction?

The best-of-seven format was introduced to the Stanley Cup Final in 1939, so 20 of the Canadiens’ 24 Stanley Cups were won by the champion after securing four wins. 

The best-of-seven format was introduced to every playoff round in 1987, and the Canadiens’ only Stanley Cup victory since then was in 1993, when they beat the Los Angeles Kings. 

Last Time the Canadiens Won the Stanley Cup 

The Canadiens last won the Stanley Cup in 1993, beating the Kings in five games.