| Year | Winning Team | Coach | Finalist | Coach |
| 2004 | Tampa Bay Lightning | John Tortorella | Calgary Flames | Darryl Sutter |
| 2003 | New Jersey Devils | Pat Burns | Mighty Ducks of Anaheim | Mike Babcock |
| 2002 | Detroit Red Wings | Scotty Bowman | Carolina Hurricanes | Paul Maurice |
| 2001 | Colorado Avalanche | Bob Hartley | New Jersey Devils | Larry Robinson |
| 2000 | New Jersey Devils | Larry Robinson | Dallas Stars | Ken Hitchcock |
| 1999 | Dallas Stars | Ken Hitchcock | Buffalo Sabres | Lindy Ruff |
| 1998 | Detroit Red Wings | Scotty Bowman | Washington Capitals | Ron Wilson |
| 1997 | Detroit Red Wings | Scotty Bowman | Philadelphia Flyers | Terry Murray |
| 1996 | Colorado Avalanche | Marc Crawford | Florida Panthers | Doug MacLean |
| 1995 | New Jersey Devils | Jacques Lemaire | Detroit Red Wings | Scotty Bowman |
| 1994 | New York Rangers | Mike Keenan | Vancouver Canucks | Pat Quinn |
| 1993 | Montreal Canadiens | Jacques Demers | Los Angeles Kings | Barry Melrose |
| 1992 | Pittsburgh Penguins | Scotty Bowman | Chicago Blackhawks | Mike Keenan |
| 1991 | Pittsburgh Penguins | Bob Johnson | Minnesota North Stars | Bob Gainey |
| 1990 | Edmonton Oilers | John Muckler | Boston Bruins | Mike Milbury |
| 1989 | Calgary Flames | Terry Crisp | Montreal Canadiens | Pat Burns |
| 1988 | Edmonton Oilers | Glen Sather | Boston Bruins | Terry O'Reilly |
| 1987 | Edmonton Oilers | Glen Sather | Philadelphia Flyers | Mike Keenan |
| 1986 | Montreal Canadiens | Jean Perron | Calgary Flames | Bob Johnson |
| 1985 | Edmonton Oilers | Glen Sather | Philadelphia Fyers | Mike Keenan |
| 1984 | Edmonton Oilers | Glen Sather | New York Islanders | Al Arbour |
| 1983 | New York Islanders | Al Arbour | Edmonton Oilers | Glen Sather |
| 1982 | New York Islanders | Al Arbour | Vancouver Canucks | Roger Neilson |
| 1981 | New York Islanders | Al Arbour | Minnesota North Stars | Glen Sonmor |
| 1980 | New York Islanders | Al Arbour | Philadelphia Flyers | Pat Quinn |
| 1979 | Montreal Canadiens | Scotty Bowman | New York Rangers | Fred Shero |
| 1978 | Montreal Canadiens | Scotty Bowman | Boston Bruins | Don Cherry |
| 1977 | Montreal Canadiens | Scotty Bowman | Boston Bruins | Don Cherry |
| 1976 | Montreal Canadiens | Scotty Bowman | Philadelphia Flyers | Fred Shero |
| 1975 | Philadelphia Flyers | Fred Shero | Buffalo Sabres | Floyd Smith |
| 1974 | Philadelphia Flyers | Fred Shero | Boston Bruins | A. 'Bep' Guidolin |
| 1973 | Montreal Canadiens | Scotty Bowman | Chicago Blackhawks | Billy Reay |
| 1972 | Boston Bruins | Tom Johnson | New York Rangers | Emile Francis |
| 1971 | Montreal Canadiens | Al MacNeil | Chicago Blackhawks | Billy Reay |
| 1970 | Boston Bruins | Harry Sinden | St. Louis Blues | Scotty Bowman |
| 1969 | Montreal Canadiens | Claude Ruel | St. Louis Blues | Scotty Bowman |
| 1968 | Montreal Canadiens | Hector 'Toe' Blake | St. Louis Blues | Scotty Bowman |
| 1967 | Toronto Maple Leafs | G. 'Punch' Imlach | Montreal Canadiens | Hector 'Toe' Blake |
| 1966 | Montreal Canadiens | Hector 'Toe' Blake | Detroit Red Wings | Sid Abel |
| 1965 | Montreal Canadiens | Hector 'Toe' Blake | Chicago Blackhawks | Billy Reay |
| 1964 | Toronto Maple Leafs | G. 'Punch' Imlach | Detroit Red Wings | Sid Abel |
| 1963 | Toronto Maple Leafs | G. 'Punch' Imlach | Detroit Red Wings | Sid Abel |
| 1962 | Toronto Maple Leafs | G. 'Punch' Imlach | Chicago Blackhawks | Rudy Pilous |
| 1961 | Chicago Blackhawks | Rudy Pilous | Detroit Red Wings | Sid Abel |
| 1960 | Montreal Canadiens | Hector 'Toe' Blake | Toronto Maple Leafs | G. 'Punch' Imlach |
| 1959 | Montreal Canadiens | Hector 'Toe' Blake | Toronto Maple Leafs | G. 'Punch' Imlach |
| 1958 | Montreal Canadiens | Hector 'Toe' Blake | Boston Bruins | Milt Schmidt |
| 1957 | Montreal Canadiens | Hector 'Toe' Blake | Boston Bruins | Milt Schmidt |
| 1956 | Montreal Canadiens | Hector 'Toe' Blake | Detroit Red Wings | Jimmy Skinner |
| 1955 | Detroit Red Wings | Jimmy Skinner | Montreal Canadiens | Dick Irvin |
| 1954 | Detroit Red Wings | Tommy Ivan | Montreal Canadiens | Dick Irvin |
| 1953 | Montreal Canadiens | Dick Irvin | Boston Bruins | Lynn Patrick |
| 1952 | Detroit Red Wings | Tommy Ivan | Montreal Canadiens | Dick Irvin |
| 1951 | Toronto Maple Leafs | Joe Primeau | Montreal Canadiens | Dick Irvin |
| 1950 | Detroit Red Wings | Tommy Ivan | New York Rangers | Lynn Patrick |
| 1949 | Toronto Maple Leafs | Clarence 'Hap' Day | Detroit Red Wings | Tommy Ivan |
| 1948 | Toronto Maple Leafs | Clarence 'Hap' Day | Detroit Red Wings | Tommy Ivan |
| 1947 | Toronto Maple Leafs | Clarence 'Hap' Day | Montreal Canadiens | Dick Irvin |
| 1946 | Montreal Canadiens | Dick Irvin | Boston Bruins | A. 'Dit 'Clapper |
| 1945 | Toronto Maple Leafs | Clarence 'Hap' Day | Detroit Red Wings | Jack Adams |
| 1944 | Montreal Canadiens | Dick Irvin | Chicago Blackhawks | Paul Thompson |
| 1943 | Detroit Red Wings | Jack Adams | Boston Bruins | Art Ross |
| 1942 | Toronto Maple Leafs | Clarence 'Hap' Day | Detroit Red Wings | Jack Adams |
| 1941 | Boston Bruins | R. 'Cooney' Weiland | Detroit Red Wings | Ebbie Goodfellow |
| 1940 | New York Rangers | Frank Boucher | Toronto Maple Leafs | Dick Irvin |
| 1939 | Boston Bruins | Art Ross | Toronto Maple Leafs | Dick Irvin |
| 1938 | Chicago Blackhawks | Bill Stewart | Toronto Maple Leafs | Dick Irvin |
| 1937 | Detroit Red Wings | Jack Adams | New York Rangers | Lester Patrick |
| 1936 | Detroit Red Wings | Jack Adams | Toronto Maple Leafs | Dick Irvin |
| 1935 | Montreal Maroons | Tommy Gorman | Toronto Maple Leafs | Dick Irvin |
| 1934 | Chicago Black Hawks | Tommy Gorman | Detroit Red Wings | Herbie Lewis |
| 1933 | New York Rangers | Lester Patrick | Toronto Maple Leafs | Dick Irvin |
| 1932 | Toronto Maple Leafs | Dick Irvin | New York Rangers | Lester Patrick |
| 1931 | Montreal Canadiens | Cecil Hart | Chicago Black Hawks | Dick Irvin |
| 1930 | Montreal Canadiens | Cecil Hart | Boston Bruins | Art Ross |
| 1929 | Boston Bruins | Cy Denneny | New York Rangers | Lester Patrick |
| 1928 | New York Rangers | Lester Patrick | Montreal Maroons | Eddie Gerard |
| 1927 | Ottawa Senators | Dave Gill | Boston Bruins | Art Ross |
| The NHL assumed control of Stanley Cup competition after 1926 |
| 1926 | Montreal Maroons | Eddie Gerard | Victoria Cougars | Lester Patrick |
| 1925 | Victoria Cougars | Lester Patrick | Montreal Canadiens | Leo Dandurand |
| 1924 | Montreal Canadiens | Leo Dandurand | Calgary Tigers
Vancouver Maroons | Eddie Oatman
Art Duncan/Frank Patrick |
| 1923 | Ottawa Senators | Pete Green | Edmonton Eskimos
Vancouver Maroons | Ken McKenzine
Lloyd Cook/Frank Patrick |
| 1922 | Toronto St. Pats | George O'Donoghue | Vancouver Millionaires | Lloyd Cook/Frank Patrick |
| 1921 | Ottawa Senators | Pete Green | Vancouver Millionaires | Lloyd Cook/Frank Patrick |
| 1920 | Ottawa Senators | Pete Green | Seattle Metropolitans | Pete Muldoon |
| 1919 | No decision | Series beween Montreal and Seattle cancelled due to influenza epidemic |
| 1918 | Toronto Arenas | Dick Carroll | Vancouver Millionaires | Frank Patrick |
| 1917 | Seattle Metropolitans | Pete Muldoon | Montreal Canadiens | Newsy Lalonde |
| 1916 | Montreal Canadiens | Newsy Lalonde | Portland Rosebuds | E.H. Savage (manager) |
| 1915 | Vancouver Millionaires | Frank Patrick | Ottawa Senators>td> | Frank Shaughnessy (manager) |
| 1914 | Toronto Blueshirts | Scotty Davidson | Victoria Cougars
Montreal Canadiens | Lester Patrick
Jimmy Gardner |
| 1913 | Quebec Bulldogs | Joe Malone (captain) | Sydney Miners | |
| 1912 | Quebec Bulldogs | Mike Quinn | Moncton Victories | |
| 1911 | Ottawa Senators | Bruce Stuart (captain) | Port Arthur Bearcats
Galt |
|
| 1910 | Montreal Wanderers
Ottawa Senators | Pud Glass (captain)
Bruce Stuart (captain) | Berlin Union Jacks
Edmonton Eskimos
Galt |
|
| 1909 | Ottawa Senators | Bruce Stuart (captain) | (no challengers) | |
| 1908 | Montreal Wanderers | Cecil Blachford | Edmonton Eskimos
Toronto Trolley Leaguers
Winnipeg Maple Leafs
Ottawa Victorias |
|
| 1907 | Montreal Wanderers
Kenora Thistles | Cecil Blachford
Tommy Phillips (captain) | Kenora Thistles
Brandon Wheat Kings
Montreal Wanderers |
|
| 1906 | Montreal Wanderers
Ottawa Silver Seven | Cecil Blachford (captain)
A.T. Smith (manager) | New Glascow Cubs
Ottawa Silver Seven
Montreal Wanderers
Smiths Falls
Queen's University |
|
| 1905 | Ottawa Silver Seven | A.T. Smith (manager) | Rat Portage Thistles
Dawson City Nuggets |
|
| 1904 | Ottawa Silver Seven | A.T. Smith (manager) | Brandon Wheat Kings
Montreal Wanderers
Toronto Marlboros
Winnipeg Rowing Club |
|
| 1903 | Ottawa Silver Seven
Montreal AAA | A.T. Smith (manager)
Clare McKerrow | Rat Portage Thistles
Montreal Victorias
Winnipeg Victorias |
|
| 1902 | Montreal AAA
Winnipeg Victorias | Clare McKerrow
| Winnipeg Victorias
Toronto Wellingtons |
|
| 1901 | Winnipeg Victorias | Dan Bain (captain) | Montreal Shamrocks | |
| 1900 | Montreal Shamrocks | Harry Trihey (captain) | Halifax Crescents
Winnipeg Victorias |
|
| 1899 | Montreal Shamrocks
Montreal Victorias | Harry Trihey (captain)
| Queen's University
Winnipeg Victorias |
|
| 1898 | Montreal Victorias | Frank Richardson (manager) | (no challengers) | |
| 1897 | Montreal Victorias | Mike Grant (captain) | Ottawa Capitals | |
| 1896 | Montreal Victorias
Winnipeg Victorias | Mike Grant (captain)
Jack Armytage (manager) | Winnipeg Victorias
Montreal Victorias |
|
| 1895 | Montreal Victorias | Mike Grant (captain) | (no challengers) | |
| 1894 | Montreal AAA | | Ottawa Generals | |
| 1893 | Montreal AAA | | (no challengers) | |
