The Stanley Cup was first awarded decades before the NHL was created. They awarded the cup differently then. From 1892 until 1914 they did not have a round robin playoff series like they do now. The winners of series could challenge each other for the Cup. Some challenges were played in the middle of the season as long as it was approved by the Stanley Cup trustees. Therefore, there was usually more than one challenge in a season, which in turn means the Cup was awarded more than once in a season.
1893
Montreal AAA
1894
Montreal AAA
1895
Montreal Victorias
1896
Montreal Victorias
1896
Winnipeg Victorias
1897
Montreal Victorias
1898
Montreal Victorias
1899
Montreal Shamrocks
1900
Montreal Shamrocks
1901
Winnipeg Victorias
1902
Winnipeg Victorias
1902
Montreal AAA
1903
Montreal AAA
1903
Ottawa Senators
1904
Ottawa Senators
1905
Ottawa Senators
1906
Ottawa Senators
1906
Montreal Wanderers
1907
Kenora Thistles
1907
Montreal Wanderers
1908
Montreal Wanderers
1909
Ottawa Senators
1910
Montreal Wanderers
1911
Ottawa Senators
1912
Quebec Bulldogs
1913
Quebec Bulldogs
1914
Toronto Blueshirts
Between 1915 and 1927, prior to the NHL taking over the Cup, they played the best of 3 or best of 5. It was usually the winner of the NHA or NHL against one of the other leagues (Western Canada Hockey League, Western Hockey League, or Pacific Coast Hockey Association).
1915
Vancouver Millionaires
1916
Montreal Canadiens
1917
Seattle Metropolitans
1918
Toronto Arenas
1919
Series Cancelled
1920
Ottawa Senators
1921
Ottawa Senators
1922
Toronto St. Pats
1923
Ottawa Senators
1924
Montreal Canadiens
1925
Victoria Cougars
1926
Montreal Maroons
The NHL officially took over the Stanley Cup in the 1926-27 season and awarded it to their annual champion.
1927
Ottawa Senators
1928
New York Rangers
1929
Boston Bruins
1930
Montreal Canadiens
1931
Montreal Canadiens
1932
1933
New York Rangers
1934
Chicago Black Hawks
1935
Montreal Maroons
1936
Detroit Red Wings
1937
Detroit Red Wings
1938
Chicago Blackhawks
1939
Boston Bruins
1940
New York Rangers
1941
Boston Bruins
1942
Toronto Maple Leafs
1943
Detroit Red Wings
1944
Montreal Canadiens
1945
Toronto Maple Leafs
1946
Montreal Canadiens
1947
Toronto Maple Leafs
1948
Toronto Maple Leafs
1949
Toronto Maple Leafs
1950
Detroit Red Wings
1951
Toronto Maple Leafs
1952
Detroit Red Wings
1953
Montreal Canadiens
1954
Detroit Red Wings
1955
Detroit Red Wings
1956
Montreal Canadiens
1957
Montreal Canadiens
1958
Montreal Canadiens
1959
Montreal Canadiens
1960
Montreal Canadiens
1961
Chicago Blackhawks
1962
Toronto Maple Leafs
1963
Toronto Maple Leafs
1964
Toronto Maple Leafs
1965
Montreal Canadiens
1966
Montreal Canadiens
1967
Toronto Maple Leafs
1968
Montreal Canadiens
1969
Montreal Canadiens
1970
Boston Bruins
1971
Montreal Canadiens
1972
Boston Bruins
1973
Montreal Canadiens
1974
1975
Philadelphia Flyers
1976
Montreal Canadiens
1977
Montreal Canadiens
1978
Montreal Canadiens
1979
Montreal Canadiens
1980
New York Islanders
1981
New York Islanders
1982
New York Islanders
1983
New York Islanders
1984
Edmonton Oilers
1985
Edmonton Oilers
1986
Montreal Canadiens
1987
Edmonton Oilers
1988
Edmonton Oilers
1989
Calgary Flames
1990
Edmonton Oilers
1991
Pittsburgh Penguins
1992
Pittsburgh Penguins
1993
Montreal Canadiens
1994
New York Rangers
1995
New Jersey Devils
1996
Colorado Avalanche
1997
Detroit Red Wings
1998
Detroit Red Wings
1999
Dallas Stars
2000
New Jersey Devils
2001
Colorado Avalanche
2002
Detroit Red Wings
2003
New Jersey Devils
2004
Tampa Bay Lightning
2005
NHL Lockout
2006
2007
Anaheim Ducks
2008
Detroit Red Wings
2009
Pittsburgh Penguins
2010
Chicago Blackhawks
2011
Boston Bruins2012
Los Angeles Kings
2013 Chicago Blackhawks
The Montreal Canadiens have won 24 Stanley Cups.
13
Montreal canadians have won the Stanley |Cup 24 times, the most in history and seriously...who cares about the cfl
he did not buy it, the cup (trophy) was made to honour him by calling it the "Stanley Cup" to be presented to the winning NHL hockey team. It was a changle trophy that started out in the late 1800s, the NHL never started until 1917.And he did buy it back thenfor all of Canada that had hockey teams. in the Early years teams from the USA even won it a time or two
The following Canadian NHL teams have won the Stanley Cup:Montreal CanadiensToronto Maple LeafsEdmonton OilersCalgary FlamesOlder teams:Ottawa Senators (not current expansion team)Montreal MaroonsVancouver MillionairesVictoria CougarsEdmonton EskimosCalgary Tigers
No one. The Stanley Cup was not invented yet.
27 different teams
No one. The Stanley Cup was awarded for the first time in 1893.
The Montreal Canadiens have won 24 Stanley Cups.
Boston Bruins
the Edmonton Oilers
13
Toronto has won more Stanley Cups, having won 13 Stanley Cups.The original Ottawa Senators have won the Stanley Cup 5 times, but the current Ottawa Senators have not yet won the Stanley cup.
The NHL expanded from six teams to twelve teams in the 1967-68. All six of the 'original' teams have won a Cup. Of the six new teams, the Los Angeles Kings and St. Louis Blues have not won a Stanley Cup. As of the 2007-08 season, they would be the oldest teams not to have won a Cup.
They won 24 cups
None. The Stanley Cup was previously awarded to the Canadian hockey champion, and later to the champion of the National Hockey League. It has never been a stake in a competition between national teams from any country.
The Montreal Canadians won more Stanley Cup victories than any other team with 24 wins.