Year
|
Winner
|
Loser
|
1941
|
Boston Bruins
|
Detroit Red Wings
|
1940
|
New York Rangers
|
Toronto Maple Leafs
|
1939
|
Boston Bruins
|
Toronto Maple Leafs
|
1938
|
Chicago Black Hawks
|
Toronto Maple Leafs
|
1937
|
Detroit Red Wings
|
New York Rangers
|
1936
|
Detroit Red Wings
|
Toronto Maple Leafs
|
1935
|
Montreal Maroons
|
Toronto Maple Leafs
|
1934
|
Chicago Black Hawks
|
Detroit Red Wings
|
1933
|
New York Rangers
|
Toronto Maple Leafs
|
1932
|
Toronto Maple Leafs
|
New York Rangers
|
1931
|
Montreal Canadiens
|
Chicago Black Hawks
|
1930
|
Montreal Canadiens
|
Boston Bruins
|
1929
|
Boston Bruins
|
New York Rangers
|
1928
|
New York Rangers
|
Montreal Maroons
|
1927
|
Ottawa Senators
|
Boston Bruins
|
1926
|
Montreal Maroons
|
Victoria Cougars
|
1925**
|
Victoria Cougars
|
Montreal Canadiens
|
1924
|
Montreal Canadiens
|
Calgary Tigers
|
1923
|
Ottawa Senators
|
Edmonton Eskimos
|
1922
|
Toronto St. Patricks
|
Vancouver Millionaires
|
1921
|
Ottawa Senators
|
Vancouver Millionaires
|
1920
|
Ottawa Senators
|
Seattle Metropolitans
|
1919*
|
Cancelled
|
Cancelled
|
1918
|
Toronto Arenas
|
Vancouver Millionaires
|
1917
|
Seattle Metropolitans
|
Montreal Canadiens
|
1916
|
Montreal Canadiens
|
Portland Rosebuds
|
1915
|
Vancouver Millionaires
|
Ottawa Senators
|
1914
|
Toronto Hockey Club (Blueshirts)
|
Victoria Aristocrats
|
1914***
|
Toronto Hockey Club (Blueshirts)
|
Montreal Canadiens
|
1913
|
Quebec Bulldogs
|
Sydney Millionaires
|
1913
|
Quebec Bulldogs
|
None (League Champion)
|
1912
|
Quebec Bulldogs
|
Moncton Victorias
|
1912
|
Quebec Bulldogs
|
None (League Champion)
|
1911
|
Ottawa Hockey Club (Senators)
|
Port Arthur Bearcats
|
1911
|
Ottawa Hockey Club (Senators)
|
Galt Hockey Club (Professionals)
|
1911
|
Ottawa Hockey Club (Senators)
|
None (League Champion)
|
1910
|
Montreal Wanderers
|
Berlin Dutchmen
|
1910
|
Montreal Wanderers
|
None (League Champion)
|
1910
|
Ottawa Hockey Club (Senators)
|
Edmonton Hockey Club (Thistles)
|
1910
|
Ottawa Hockey Club (Senators)
|
Galt Hockey Club (Professionals)
|
1909
|
Ottawa Hockey Club (Senators)
|
None (League Champion)
|
1908
|
Montreal Wanderers
|
Edmonton Hockey Club (Thistles)
|
1908
|
Montreal Wanderers
|
Toronto Hockey Club (Blueshirts)
|
1908
|
Montreal Wanderers
|
Winnipeg Maple Leafs
|
1908
|
Montreal Wanderers
|
None (League Champion)
|
1908
|
Montreal Wanderers
|
Ottawa Victorias
|
1907
|
Montreal Wanderers
|
Kenora Thistles
|
1907
|
Kenora Thistles
|
Wheat City Hockey Club
|
1907
|
Kenora Thistles
|
Montreal Wanderers
|
1906
|
Montreal Wanderers
|
New Glasgow Cubs
|
1906
|
Montreal Wanderers
|
Ottawa Hockey Club (Silver Sevens)
|
1906
|
Ottawa Hockey Club (Silver Sevens)
|
Smiths Falls Hockey Club
|
1906
|
Ottawa Hockey Club (Silver Sevens)
|
Queen's University
|
1905
|
Ottawa Hockey Club (Silver Sevens)
|
Rat Portage Thistles
|
1905
|
Ottawa Hockey Club (Silver Sevens)
|
Dawson City Nuggets
|
1905
|
Ottawa Hockey Club (Silver Sevens)
|
None (League Champion)
|
1904
|
Ottawa Hockey Club (Silver Sevens)
|
Wheat City Hockey Club
|
1904
|
Ottawa Hockey Club (Silver Sevens)
|
Montreal Wanderers
|
1903-1904
|
Ottawa Hockey Club (Silver Sevens)
|
Winnipeg Rowing Club
|
1903
|
Ottawa Hockey Club (Silver Sevens)
|
Rat Portage Thistles
|
1903
|
Ottawa Hockey Club (Silver Sevens)
|
Toronto Marlboros
|
1903
|
Ottawa Hockey Club (Silver Sevens)
|
Montreal Victorias
|
1903
|
Montreal Hockey Club (AAA Winged Wheelers)
|
Winnipeg Victorias
|
1902
|
Montreal Hockey Club (AAA Winged Wheelers)
|
Winnipeg Victorias
|
1902
|
Winnipeg Victorias
|
None (League Champion)
|
1902
|
Winnipeg Victorias
|
Toronto Wellingtons
|
1901
|
Winnipeg Victorias
|
Montreal Shamrocks
|
1900
|
Montreal Shamrocks
|
None (League Champion)
|
1900
|
Montreal Shamrocks
|
Halifax Crescents
|
1900
|
Montreal Shamrocks
|
Winnipeg Victorias
|
1899
|
Montreal Shamrocks
|
Queen's University
|
1899
|
Montreal Shamrocks
|
None (League Champion)
|
1899
|
Montreal Victorias
|
Winnipeg Victorias
|
1898
|
Montreal Victorias
|
None (League Champion)
|
1897
|
Montreal Victorias
|
Ottawa Capitals
|
1897
|
Montreal Victorias
|
None (League Champion)
|
1896
|
Montreal Victorias
|
Winnipeg Victorias
|
1896
|
Winnipeg Victorias
|
None (League Champion)
|
1896
|
Winnipeg Victorias
|
Montreal Victorias
|
1895
|
Montreal Victorias
|
None (League Champion)
|
1895
|
Montreal Hockey Club (AAA Winged Wheelers)
|
Queen's University
|
1894
|
Montreal Hockey Club (AAA Winged Wheelers)
|
Ottawa Hockey Club (Generals)
|
1893
|
Montreal Hockey Club (AAA Winged Wheelers
|
None (League Champion)
|