The Stanley Cup has been awarded to the NHL's champion every year since 1927 (with one exception). From 1915 to 1926, it was awarded to the winner of the NHL/NHA vs. PCHA/WCHL/WHL championship series (with one exception), and prior to that (1893-1914), it went to the winner of the Challenge Cup in Canada. Put another way: There is a lot of history behind the Stanley Cup. With the 2023 Stanley Cup Final now complete, here is a list of every Cup winner and runner-up, along with the player who was awarded the Conn Smythe Trophy as MVP of the postseason (beginning in 1965).
2023: Vegas Golden Knights
Losing team: Florida Panthers
Conn Smythe: Jonathan Marchessault, RW, Golden Knights 2022: Colorado Avalanche
Losing team: Tampa Bay Lightning
Conn Smythe: Cale Makar, D, Avalanche 2021: Tampa Bay Lightning
Losing team: Montreal Canadiens
Conn Smythe: Andrei Vasilevskiy, G, Lightning 2020: Tampa Bay Lightning
Losing team: Dallas Stars
Conn Smythe: Victor Hedman, D, Lightning 2019: St. Louis Blues
Losing team: Boston Bruins
Conn Smythe: Ryan O'Reilly, C, Blues 2018: Washington Capitals
Losing team: Vegas Golden Knights
Conn Smythe: Alex Ovechkin, LW, Capitals 2017: Pittsburgh Penguins
Losing team: Nashville Predators
Conn Smythe: Sidney Crosby, C, Penguins 2016: Pittsburgh Penguins
Losing team: San Jose Sharks
Conn Smythe: Sidney Crosby, C, Penguins 2015: Chicago Blackhawks
Losing team: Tampa Bay Lightning
Conn Smythe: Duncan Keith, D, Blackhawks 2014: Los Angeles Kings
Losing team: New York Rangers
Conn Smythe: Justin Williams, RW, Kings 2013: Chicago Blackhawks
Losing team: Boston Bruins
Conn Smythe: Patrick Kane, RW, Blackhawks 2012: Los Angeles Kings
Losing team: New Jersey Devils
Conn Smythe: Jonathan Quick, G, Kings 2011: Boston Bruins
Losing team: Vancouver Canucks
Conn Smythe: Tim Thomas, G, Bruins 2010: Chicago Blackhawks
Losing team: Philadelphia Flyers
Conn Smythe: Jonathan Toews, C, Blackhawks 2009: Pittsburgh Penguins
Losing team: Detroit Red Wings
Conn Smythe: Evgeni Malkin, C, Penguins 2008: Detroit Red Wings
Losing team: Pittsburgh Penguins
Conn Smythe: Henrik Zetterberg, C, Red Wings 2007: Anaheim Ducks
Losing team: Ottawa Senators
Conn Smythe: Scott Niedermayer, D, Ducks 2006: Carolina Hurricanes
Losing team: Edmonton Oilers
Conn Smythe: Cam Ward, G, Hurricanes 2005: Cancelled: Season-long lockout 2004: Tampa Bay Lightning
Losing team: Calgary Flames
Conn Smythe: Brad Richards, C, Lightning 2003: New Jersey Devils
Losing team: Mighty Ducks of Anaheim
Conn Smythe: Jean-Sebastien Giguere, G, Mighty Ducks 2002: Detroit Red Wings
Losing team: Carolina Hurricanes
Conn Smythe: Nicklas Lidstrom, D, Red Wings 2001: Colorado Avalanche
Losing team: New Jersey Devils
Conn Smythe: Patrick Roy, G, Avalanche 2000: New Jersey Devils
Losing team: Dallas Stars
Conn Smythe: Scott Stevens, D, Devils 1999: Dallas Stars
Losing team: Buffalo Sabres
Conn Smythe: Joe Nieuwendyk, C, Stars 1998: Detroit Red Wings
Losing team: Washington Capitals
Conn Smythe: Steve Yzerman, C, Red Wings 1997: Detroit Red Wings
Losing team: Philadelphia Flyers
Conn Smythe: Mike Vernon, G, Red Wings 1996: Colorado Avalanche
Losing team: Florida Panthers
Conn Smythe: Joe Sakic, C, Avalanche 1995: New Jersey Devils
Losing team: Detroit Red Wings
Conn Smythe: Claude Lemieux, RW, Devils 1994: New York Rangers
Losing team: Vancouver Canucks
Conn Smythe: Brian Leetch, D, Rangers 1993: Montreal Canadiens
Losing team: Los Angeles Kings
Conn Smythe: Patrick Roy, G, Canadiens 1992: Pittsburgh Penguins
Losing team: Chicago Blackhawks
Conn Smythe: Mario Lemieux, C, Penguins 1991: Pittsburgh Penguins
Losing team: Minnesota North Stars
Conn Smythe: Mario Lemieux, C, Penguins 1990: Edmonton Oilers
Losing team: Boston Bruins
Conn Smythe: Bill Ranford, G, Oilers 1989: Calgary Flames
Losing team: Montreal Canadiens
Conn Smythe: Al MacInnis, D, Flames 1988: Edmonton Oilers
Losing team: Boston Bruins
Conn Smythe: Wayne Gretzky, C, Oilers 1987: Edmonton Oilers
Losing team: Philadelphia Flyers
Conn Smythe: Ron Hextall, G, Flyers 1986: Montreal Canadiens
Losing team: Calgary Flames
Conn Smythe: Patrick Roy, G, Canadiens 1985: Edmonton Oilers
Losing team: Philadelphia Flyers
Conn Smythe: Wayne Gretzky, C, Oilers 1984: Edmonton Oilers
Losing team: New York Islanders
Conn Smythe: Mark Messier, C, Oilers 1983: New York Islanders
Losing team: Edmonton Oilers
Conn Smythe: Billy Smith, G, Islanders 1982: New York Islanders
Losing team: Vancouver Canucks
Conn Smythe: Mike Bossy, RW, Islanders 1981: New York Islanders
Losing team: Minnesota North Stars
Conn Smythe: Butch Goring, C, Islanders 1980: New York Islanders
Losing team: Philadelphia Flyers
Conn Smythe: Bryan Trottier, C, Islanders 1979: Montreal Canadiens
Losing team: New York Rangers
Conn Smythe: Bob Gainey, C, Canadiens 1978: Montreal Canadiens
Losing team: Boston Bruins
Conn Smythe: Larry Robinson, D, Canadiens 1977: Montreal Canadiens
Losing team: Boston Bruins
Conn Smythe: Guy Lafleur, RW, Canadiens 1976: Montreal Canadiens
Losing team: Philadelphia Flyers
Conn Smythe: Reggie Leach, RW, Flyers 1975: Philadelphia Flyers
Losing team: Buffalo Sabres
Conn Smythe: Bernie Parent, G, Flyers 1974: Philadelphia Flyers
Losing team: Boston Bruins
Conn Smythe: Bernie Parent, G, Flyers 1973: Montreal Canadiens
Losing team: Chicago Black Hawks
Conn Smythe: Yvan Cournoyer, RW, Canadiens 1972: Boston Bruins
Losing team: New York Rangers
Conn Smythe: Bobby Orr, D, Bruins 1971: Montreal Canadiens
Losing team: Chicago Black Hawks
Conn Smythe: Ken Dryden, G, Canadiens 1970: Boston Bruins
Losing team: St. Louis Blues
Conn Smythe: Bobby Orr, D, Bruins 1969: Montreal Canadiens
Losing team: St. Louis Blues
Conn Smythe: Serge Savard, D, Canadiens 1968: Montreal Canadiens
Losing team: St. Louis Blues
Conn Smythe: Glenn Hall, G, Blues 1967: Toronto Maple Leafs
Losing team: Montreal Canadiens
Conn Smythe: Dave Keon, C, Maple Leafs 1966: Montreal Canadiens
Losing team: Detroit Red Wings
Conn Smythe: Roger Crozier, G, Red Wings 1965: Montreal Canadiens
Losing team: Chicago Black Hawks
Conn Smythe: Jean Beliveau, C, Canadiens 1964: Toronto Maple Leafs
Losing team: Detroit Red Wings 1963: Toronto Maple Leafs
Losing team: Detroit Red Wings 1962: Toronto Maple Leafs
Losing team: Chicago Black Hawks 1961: Chicago Black Hawks
Losing team: Detroit Red Wings 1960: Montreal Canadiens
Losing team: Toronto Maple Leafs 1959: Montreal Canadiens
Losing team: Toronto Maple Leafs 1958: Montreal Canadiens
Losing team: Boston Bruins 1957: Montreal Canadiens
Losing team: Boston Bruins 1956: Montreal Canadiens
Losing team: Detroit Red Wings 1955: Detroit Red Wings
Losing team: Montreal Canadiens 1954: Detroit Red Wings
Losing team: Montreal Canadiens 1953: Montreal Canadiens
Losing team: Boston Bruins 1952: Detroit Red Wings
Losing team: Montreal Canadiens 1951: Toronto Maple Leafs
Losing team: Montreal Canadiens 1950: Detroit Red Wings
Losing team: New York Rangers 1949: Toronto Maple Leafs
Losing team: Detroit Red Wings 1948: Toronto Maple Leafs
Losing team: Detroit Red Wings 1947: Toronto Maple Leafs
Losing team: Montreal Canadiens 1946: Montreal Canadiens
Losing team: Boston Bruins 1945: Toronto Maple Leafs
Losing team: Detroit Red Wings 1944: Montreal Canadiens
Losing team: Chicago Black Hawks 1943: Detroit Red Wings
Losing team: Boston Bruins 1942: Toronto Maple Leafs
Losing team: Detroit Red Wings 1941: Boston Bruins
Losing team: Detroit Red Wings 1940: New York Rangers
Losing team: Toronto Maple Leafs 1939: Boston Bruins
Losing team: Toronto Maple Leafs 1938: Chicago Black Hawks
Losing team: Toronto Maple Leafs 1937: Detroit Red Wings
Losing team: New York Rangers 1936: Detroit Red Wings
Losing team: Toronto Maple Leafs 1935: Montreal Maroons
Losing team: Toronto Maple Leafs 1934: Chicago Black Hawks
Losing team: Detroit Red Wings 1933: New York Rangers
Losing team: Toronto Maple Leafs 1932: Toronto Maple Leafs
Losing team: New York Rangers 1931: Montreal Canadiens
Losing team: Chicago Black Hawks 1930: Montreal Canadiens
Losing team: Boston Bruins 1929: Boston Bruins
Losing team: New York Rangers 1928: New York Rangers
Losing team: Montreal Maroons 1927: Ottawa Senators
Losing team: Boston Bruins 1926: Montreal Maroons
Losing team: Victoria Cougars 1925: Victoria Cougars
Losing team: Montreal Canadiens 1924: Montreal Canadiens
Losing team: Calgary Tigers 1923: Ottawa Senators
Losing team: Edmonton Eskimos 1922: Toronto St. Patricks
Losing team: Vancouver Millionaires 1921: Ottawa Senators
Losing team: Vancouver Millionaires 1920: Ottawa Senators
Losing team: Seattle Metropolitans 1919: Cancelled: Influenza epidemic 1918: Toronto Hockey Club
Losing team: Vancouver Millionaires 1917: Seattle Metropolitans
Losing team: Montreal Canadiens 1916: Montreal Canadiens
Losing team: Portland Rosebuds 1915: Vancouver Millionaires
Losing team: Ottawa Senators
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