1992-93 - Montreal Canadiens
1989-90 - Edmonton Oilers
before that The "Hab's" pretty much ruled the game...with the Leaf's....
most wins since NHL formed:
NHL Winners:
Montreal Canadiens: 23
(The Canadiens also have one pre-NHL win, listed below)
1924, 1930, 1931, 1944, 1946, 1953, 1956, 1957, 1958, 1959, 1960, 1965, 1966, 1968, 1969, 1971, 1973, 1976, 1977, 1978, 1979, 1986, 1993
Toronto Maple Leafs: 13
(Includes wins under previous franchise names: Toronto Arenas and Toronto St. Pats)
1918, 1922, 1932, 1942, 1945, 1947, 1948, 1949, 1951, 1962, 1963, 1964, 1967
Detroit Red Wings: 11
1936, 1937, 1943, 1950, 1952, 1954, 1955, 1997, 1998, 2002, 2008
Edmonton Oilers: 5
1984, 1985, 1987, 1988, 1990
Boston Bruins: 5
1929, 1939, 1941, 1970, 1972
Chicago Blackhawks: 4
1934, 1938, 1961, 2010
New York Rangers: 4
1928, 1933, 1940, 1994
New York Islanders: 4
1980, 1981, 1982, 1983
Ottawa Senators: 4
(The Senators also have six pre-NHL wins, listed below)
1920, 1921, 1923, 1927
Pittsburgh Penguins: 3
1991, 1992, 2009
New Jersey Devils: 3
1995, 2000, 2003
Colorado Avalanche: 2
1996, 2001
Philadelphia Flyers: 2
1974, 1975
Montreal Maroons: 2
1926, 1935
Anaheim Ducks: 1
2007
Carolina Hurricanes: 1
2006
Tampa Bay Lightning: 1
2004
Dallas Stars: 1
1999
Calgary Flames: 1
1989
Victoria Cougars: 1
1925
fyi:
The Toronto Maple Leafs' Stanley Cup drought continues, with no championship since 1967. That's the longest Stanley Cup drought among teams that have won it at least once.
