Posts
| Year | Champion | Cups | GP | Winning GM | Winning Coach | Final Opponent |
| 2009 | Pittsburgh Penguins | 3 | 5 | Ray Shero | Dan Bylsma | Detroit Red Wings |
| 2008 | Detroit Red Wings | 11 | 6 | Ken Holland | Mike Babcock | Pittsburgh Penguins |
| 2007 | Anaheim Ducks | 1 | 5 | Brian Burke | Randy Carlyle | Ottawa Senators |
| 2006 | Carolina Hurricanes | 1 | 7 | Jim Rutherford | Peter Laviolette | Edmonton Oilers |
| 2004 | Tampa Bay Lightning | 1 | 7 | Jay Feaster | John Tortorella | Calgary Flames |
| 2003 | New Jersey Devils | 3 | 7 | Lou Lamoriello | Pat Burns | Mighty Ducks of Anaheim |
| 2002 | Detroit Red Wings | 10 | 5 | Ken Holland | Scotty Bowman | Carolina Hurricanes |
| 2001 | Colorado Avalanche | 2 | 7 | Pierre Lacroix | Bob Hartley | New Jersey Devils |
| 2000 | New Jersey Devils | 2 | 6 | Lou Lamoriello | Larry Robinson | Dallas Stars |
| 1999 | Dallas Stars | 1 | 6 | Bob Gainey | Ken Hitchcock | Buffalo Sabres |
| 1998 | Detroit Red Wings | 9 | 4 | Ken Holland | Scotty Bowman | Washington Capitals |
| 1997 | Detroit Red Wings | 8 | 4 | Scotty Bowman | Scotty Bowman | Philadelphia Flyers |
| 1996 | Colorado Avalanche | 1 | 4 | Pierre Lacroix | Marc Crawford | Florida Panthers |
| 1995 | New Jersey Devils | 1 | 4 | Lou Lamoriello | Jacques Lemaire | Detroit Red Wings |
| 1994 | New York Rangers | 4 | 7 | Neil Smith | Mike Keenan | Vancouver Canucks |
| 1993 | Montreal Canadiens | 24 | 5 | Serge Savard | Jacques Demers | Los Angeles Kings |
| 1992 | Pittsburgh Penguins | 2 | 4 | Craig Patrick | Scotty Bowman | Chicago Black Hawks |
| 1991 | Pittsburgh Penguins | 1 | 6 | Craig Patrick | Bob Johnson | Minnesota North Stars |
| 1990 | Edmonton Oilers | 5 | 5 | Glen Sather | John Muckler | Boston Bruins |
| 1989 | Calgary Flames | 1 | 6 | Cliff Fletcher | Terry Crisp | Montreal Canadiens |
| 1988 | Edmonton Oilers | 4 | 4 | Glen Sather | Glen Sather | Boston Bruins |
| 1987 | Edmonton Oilers | 3 | 7 | Glen Sather | Glen Sather | Philadelphia Flyers |
| 1986 | Montreal Canadiens | 23 | 5 | Serge Savard | Jean Perron | Calgary Flames |
| 1985 | Edmonton Oilers | 2 | 5 | Glen Sather | Glen Sather | Philadelphia Flyers |
| 1984 | Edmonton Oilers | 1 | 5 | Glen Sather | Glen Sather | New York Islanders |
| 1983 | New York Islanders | 4 | 4 | Bill Torrey | Al Arbour | Edmonton Oilers |
| 1982 | New York Islanders | 3 | 4 | Bill Torrey | Al Arbour | Vancouver Canucks |
| 1981 | New York Islanders | 2 | 5 | Bill Torrey | Al Arbour | Minnesota North Stars |
| 1980 | New York Islanders | 1 | 6 | Bill Torrey | Al Arbour | Philadelphia Flyers |
| 1979 | Montreal Canadiens | 22 | 5 | Irving Grundman | Scotty Bowman | New York Rangers |
| 1978 | Montreal Canadiens | 21 | 6 | Sam Pollock | Scotty Bowman | Boston Bruins |
| 1977 | Montreal Canadiens | 20 | 4 | Sam Pollock | Scotty Bowman | Boston Bruins |
| 1976 | Montreal Canadiens | 19 | 4 | Sam Pollock | Scotty Bowman | Philadelphia Flyers |
| 1975 | Philadelphia Flyers | 2 | 6 | Keith Allen | Fred Shero | Buffalo Sabres |
| 1974 | Philadelphia Flyers | 1 | 6 | Keith Allen | Fred Shero | Boston Bruins |
| 1973 | Montreal Canadiens | 18 | 6 | Sam Pollock | Scotty Bowman | Chicago Black Hawks |
| 1972 | Boston Bruins | 5 | 6 | Milt Schmidt | Tom Johnson | New York Rangers |
| 1971 | Montreal Canadiens | 17 | 7 | Sam Pollock | Al MacNeil | Chicago Black Hawks |
| 1970 | Boston Bruins | 4 | 4 | Milt Schmidt | Harry Sinden | St. Louis Blues |
| 1969 | Montreal Canadiens | 16 | 4 | Sam Pollock | Claude Ruel | St. Louis Blues |
| 1968 | Montreal Canadiens | 15 | 4 | Sam Pollock | Toe Blake | St. Louis Blues |
| 1967 | Toronto Maple Leafs | 11 | 6 | Punch Imlach | Punch Imlach | Montreal Canadiens |
| 1966 | Montreal Canadiens | 14 | 6 | Sam Pollock | Toe Blake | Detroit Red Wings |
| 1965 | Montreal Canadiens | 13 | 7 | Sam Pollock | Toe Blake | Chicago Black Hawks |
| 1964 | Toronto Maple Leafs | 10 | 7 | Punch Imlach | Punch Imlach | Detroit Red Wings |
| 1963 | Toronto Maple Leafs | 9 | 5 | Punch Imlach | Punch Imlach | Detroit Red Wings |
| 1962 | Toronto Maple Leafs | 8 | 6 | Punch Imlach | Punch Imlach | Chicago Black Hawks |
| 1961 | Chicago Black Hawks | 3 | 6 | Tommy Ivan | Rudy Pilous | Detroit Red Wings |
| 1960 | Montreal Canadiens | 12 | 4 | Frank Selke | Toe Blake | Toronto Maple Leafs |
| 1959 | Montreal Canadiens | 11 | 5 | Frank Selke | Toe Blake | Toronto Maple Leafs |
| 1958 | Montreal Canadiens | 10 | 6 | Frank Selke | Toe Blake | Boston Bruins |
| 1957 | Montreal Canadiens | 9 | 5 | Frank Selke | Toe Blake | Boston Bruins |
| 1956 | Montreal Canadiens | 8 | 5 | Frank Selke | Toe Blake | Detroit Red Wings |
| 1955 | Detroit Red Wings | 7 | 7 | Jack Adams | Jimmy Skinner | Montreal Canadiens |
| 1954 | Detroit Red Wings | 6 | 7 | Jack Adams | Tommy Ivan | Montreal Canadiens |
| 1953 | Montreal Canadiens | 7 | 5 | Frank Selke | Dick Irvin | Boston Bruins |
| 1952 | Detroit Red Wings | 5 | 4 | Jack Adams | Tommy Ivan | Montreal Canadiens |
| 1951 | Toronto Maple Leafs | 7 | 5 | Conn Smythe | Joe Primeau | Montreal Canadiens |
| 1950 | Detroit Red Wings | 4 | 7 | Jack Adams | Tommy Ivan | New York Rangers |
| 1949 | Toronto Maple Leafs | 6 | 4 | Conn Smythe | Hap Day | Detroit Red Wings |
| 1948 | Toronto Maple Leafs | 5 | 4 | Conn Smythe | Hap Day | Detroit Red Wings |
| 1947 | Toronto Maple Leafs | 4 | 6 | Conn Smythe | Hap Day | Montreal Canadiens |
| 1946 | Montreal Canadiens | 6 | 5 | Tommy Gorman | Dick Irvin | Boston Bruins |
| 1945 | Toronto Maple Leafs | 3 | 7 | Conn Smythe | Hap Day | Detroit Red Wings |
| 1944 | Montreal Canadiens | 5 | 4 | Tommy Gorman | Dick Irvin | Chicago Black Hawks |
| 1943 | Detroit Red Wings | 3 | 4 | Jack Adams | Tommy Ivan | Boston Bruins |
| 1942 | Toronto Maple Leafs | 2 | 7 | Conn Smythe | Hap Day | Detroit Red Wings |
| 1941 | Boston Bruins | 3 | 4 | Art Ross | Coony Weiland | Detroit Red Wings |
| 1940 | New York Rangers | 3 | 6 | Lester Patrick | Frank Boucher | Toronto Maple Leafs |
| 1939 | Boston Bruins | 2 | 5 | Art Ross | Art Ross | Toronto Maple Leafs |
| 1938 | Chicago Black Hawks | 2 | 4 | Bill Stewart | Bill Stewart | Toronto Maple Leafs |
| 1937 | Detroit Red Wings | 2 | 5 | Jack Adams | Jack Adams | New York Rangers |
| 1936 | Detroit Red Wings | 1 | 4 | Jack Adams | Jack Adams | Toronto Maple Leafs |
| 1935 | Montreal Maroons | 2 | 3 | Tommy Gorman | Tommy Gorman | Toronto Maple Leafs |
| 1934 | Chicago Black Hawks | 1 | 4 | Tommy Gorman | Tommy Gorman | Detroit Red Wings |
| 1933 | New York Rangers | 2 | 4 | Lester Patrick | Lester Patrick | Toronto Maple Leafs |
| 1932 | Toronto Maple Leafs | 1 | 3 | Conn Smythe | Dick Irvin | New York Rangers |
| 1931 | Montreal Canadiens | 4 | 5 | Cecil Hart | Cecil Hart | Chicago Black Hawks |
| 1930 | Montreal Canadiens | 3 | 2 | Cecil Hart | Cecil Hart | Boston Bruins |
| 1929 | Boston Bruins | 1 | 2 | Art Ross | Cy Denneny | New York Rangers |
| 1928 | New York Rangers | 1 | 5 | Lester Patrick | Lester Patrick | Montreal Maroons |
| 1927 | Ottawa Senators | 6 | 3 | Dave Gill | Dave Gill | Boston Bruins |
| 1926 | Montreal Maroons | 1 | 4 | Eddie Gerard | Eddie Gerard | Victoria Cougars |
| 1925 | Victoria Cougars | 1 | 4 | Lester Patrick | Lester Patrick | Montreal Canadiens |
| 1924 | Montreal Canadiens | 2 | 2 2 | Leo Dandurand | Leo Dandurand | Calgary Tigers Vancouver Maroons |
| 1923 | Ottawa Senators | 5 | 2 4 | Tommy Gorman | Pete Green | Edmonton Eskimos Vancouver Maroons |
| 1922 | Toronto St. Pats | 1 | 5 | Charlie Querrie | Eddie Powers | Vancouver Millionaires |
| 1921 | Ottawa Senators | 4 | 5 | Tommy Gorman | Pete Green | Vancouver Millionaires |
| 1920 | Ottawa Senators | 3 | 5 | Tommy Gorman | Pete Green | Seattle Metropolitans |
| Year | Champion | Cups | GP | Winning GM | Winning Coach | Final Opponent |
| 1918 | Toronto Arenas | 1 | 5 | ------------ | Charlie Querrie | Vancouver Millionaires |
| Year | Champion | Cups | GP | Winning GM | Winning Coach | Final Opponent |
| 1917 | Seattle Metropolitans | 1 | 4 | Pete Muldoon | Pete Muldoon | Montreal Canadiens |
| 1916 | Montreal Canadiens | 1 | 5 | George Kennedy | George Kennedy | Portland Rosebuds |
| 1915 | Vancouver Millionaires | 1 | 3 | Frank Patrick | Frank Patrick | Ottawa Senators |
| 1914 | Toronto Blueshirts | 1 | 3 2 | Jack Marshall | Scotty Davidson | Victoria Cougers Montreal Canadiens |
| 1913 | Quebec Bulldogs | 2 | 2 | M.J. Quinn | Joe Malone | Sydney Miners |
| 1912 | Quebec Bulldogs | 1 | 2 | M.J. Quinn | C. Nolan | Moncton Victorias Port Arthur Bearcats |
| 1911 | Ottawa Senators | 2 | 1 | --- | Bruce Stuart | Port Arthur Bearcats |
| 1910 | Montreal Wanderers | 4 | 1 | R.R. Boon | Pud Glass | Berlin Union Jacks |
| 1909 | Ottawa Senators | 1 | 2 | --- | Bruce Stuart | Edmonton Eskimos |
| 1908 | Montreal Wanderers | 3 | 2 2 2 2 | R.R. Boon | Cecil Blachford | Edmonton Eskimos Toronto Winnipeg Maple Leafs Ottawa Victorias |
| 1907 | Montreal Wanderers Kenora Thistles | 2 1 2 | 2 | R.R. Boon F.A. Hudson | Cecil Blachford Tommy Philips | Kenora Thistles Montreal Wanderers |
| 1906 | Montreal Wanderers Ottawa Silver Seven | 1 4 | 2 2 2 2 | --- | Cecil Blachford A.T. Smith | New Glasgow Cubs Ottawa Silver Seven Smith's Falls Queen's University |
| 1905 | Ottawa Silver Seven | 3 | 3 2 | --- | A.T. Smith | Rat Portage Thistles Dawson City Klondikers |
| 1904 | Ottawa Silver Seven | 2 | 2 2 2 1 | --- | A.T. Smith | Brandon Wheat Kings Montreal Wanderers Toronto Marlboros Winnipeg Rowing Club |
| 1903 | Ottawa Silver Seven Montreal A.A.A. | 1 4 | 2 2 4 | --- | A.T. Smith C. McKerrow | Rat Portage Thistles Montreal Victorias Winnipeg Victorias |
| 1902 | Montreal A.A.A. Winnipeg Victorias | 3 3 | 3 2 | --- | C. McKerrow D.H. Bain | Winnipeg Victorias Toronto Wellingtons |
| 1901 | Winnipeg Victorias | 2 | 2 | --- | D.H. Bain | Montreal Shamrocks |
| 1900 | Montreal Shamrocks | 2 | 5 3 | --- | H.J. Trihey | Halifax Crescents Winnipeg Victorias |
| 1899 | Montreal Shamrocks Montreal Victorias | 1 5 | 1 2 | --- | H.J. Trihey F. Richardson | Queens University Winnipeg Victorias |
| 1898 | Montreal Victorias | 4 | 4 | --- | F. Richardson | Acclaimed |
| 1897 | Montreal Victorias | 3 | 1 | --- | Mike Grant | Ottawa Capitals |
| 1896 | Montreal Victorias Winnipeg Victorias | 2 1 | 1 1 | --- | Mike Grant J.C.G. Armytage | Winnipeg Victorias Montreal Victorias |
| 1895 | Montreal Victorias | 1 | 1 | --- | Mike Grant | Acclaimed |
| 1894 | Montreal A.A.A. | 2 | 1 | --- | N/A | Ottawa Capitals |
| 1893 | Montreal A.A.A. | 1 | 1 | --- | N/A | Acclaimed |
