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 on tap, 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).
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
Source: www.espn.com