With the sprint to the Stanley Cup officially underway, here’s a look at the playoff matchups fans have seen the most of over the years.
One of the most exciting times of the year for sports is finally upon us, with the race to perhaps the most famous trophy in North American professional sports in the Stanley Cup Playoffs officially underway.
As is customary with the Stanley Cup Playoffs, 16 of the league’s 32 teams have qualified, needing that same total of wins across four best-of-seven series in order to take home the Stanley Cup – which will be given to a new winner this year, as the two-time defending champion Florida Panthers failed to make the playoffs.
While the three other major professional sports leagues all have storied traditions and extensive history when it comes to the postseason, it’s simply built a bit different in the NHL. Though the NHL wasn’t established until 1917, the Stanley Cup has been awarded since 1893 – with the trophy’s winner being decided through league play and challenge games early in its history.
The trophy became the NHL’s championship trophy by 1926, officially serving that role by 1947 – five years after the Original Six era began, which saw intense competition and rivalry between the league’s six teams at the time:
- Toronto Maple Leafs
- Montreal Canadiens
- New York Rangers
- Boston Bruins
- Detroit Red Wings
- Chicago Blackhawks
During this era, the playoffs were conducted in a semifinal/final format, allowing four of the six teams to qualify. This era continues to have a strong impact on Stanley Cup Playoffs history today, with many of the most common matchups of all-time having occurred during this period.
The league began its period of rapid growth in 1967, when the NHL doubled in size while adding teams that are well-known today such as the Pittsburgh Penguins, Los Angeles Kings, Philadelphia Flyers and St. Louis Blues. Expansion continued throughout the next several decades, culminating in the 32-team league seen today.
The NHL has operated a 16-team postseason since the absorption of World Hockey Association franchises ahead of the 1979-80 season, with the league expanding from 21 to 32 teams in the time since the playoff field was widened.
While all of the most common playoff matchups in NHL history involve Original Six franchises, the most frequent matchup involving expansion teams would be that of the Dallas Stars and St. Louis Blues, who have met in the postseason on 14 separate occasions.
Below is a look at all of the matchups that have occurred 15 or more times in Stanley Cup Playoffs history:
1. Montreal Canadiens vs. Boston Bruins: 34 matchups, Montreal leads 25-9
Montreal wins: 1930, 1931, 1946, 1947, 1952, 1953, 1954, 1955, 1957, 1958, 1968, 1969, 1971, 1977, 1978, 1979, 1984, 1985, 1986, 1987, 1989, 2002, 2004, 2008, 2014
Boston wins: 1929, 1943, 1988, 1990, 1991, 1992, 1994, 2009, 2011
2. Toronto Maple Leafs vs. Detroit Red Wings: 23 matchups, Toronto leads 12-11
Toronto wins: 1929, 1939, 1940, 1942, 1945, 1947, 1948, 1949, 1960, 1963, 1964, 1993
Detroit wins: 1934, 1936, 1943, 1950, 1952, 1954, 1955, 1956, 1961, 1987, 1988
3. (tie) Montreal Canadiens vs. Chicago Blackhawks: 17 matchups, Montreal leads 12-5
Montreal wins: 1930, 1931, 1944, 1946, 1953, 1959, 1960, 1965, 1968, 1971, 1973, 1976
Chicago wins: 1934, 1938, 1941, 1961, 1962
3. (tie) Boston Bruins vs. Toronto Maple Leafs: 17 matchups, Boston leads 9-8
Boston wins: 1939, 1941, 1969, 1972, 1974, 2013, 2018, 2019, 2024
Toronto wins: 1933, 1935, 1936, 1938, 1948, 1949, 1951, 1959
5. (tie) Montreal Canadiens vs. Toronto Maple Leafs: 16 matchups, Montreal leads 9-7
Montreal wins: 1925, 1944, 1959, 1960, 1965, 1966, 1978, 1979, 2021
Toronto wins: 1918, 1945, 1947, 1951, 1963, 1964, 1967
5. (tie) New York Rangers vs. Montreal Canadiens: 16 matchups, New York leads 9-7
New York wins: 1932, 1933, 1935, 1950, 1972, 1974, 1996, 2014, 2017
Montreal wins: 1930, 1956, 1957, 1967, 1969, 1979, 1986
5. (tie) Chicago Blackhawks vs. Detroit Red Wings: 16 matchups, Chicago leads 9-7
Chicago wins: 1934, 1944, 1961, 1965, 1970, 1985, 1989, 1992, 2013
Detroit wins: 1941, 1963, 1964, 1966, 1987, 1995, 2009
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