** indicates that the 2019-20 regular season was suspended due to the COVID-19 pandemic and that a 24-team "bubble" playoff in Canada was used to finish the season; the 2020-21 regular season was shortened to 56 games (instead of 82) and temporarily realigned divisions to put all 7 Canadian teams in one division.
* indicates NHL Presidents' Trophy winner (est. 1985) for most points in the regular season
| Season | Champion | Runner-up | Series | Winning Coach | MVP (Conn Smythe) | Losing Coach |
|---|---|---|---|---|---|---|
| 2021-22 | Colorado Avalanche 4 | Tampa Bay Lightning 2 | (WWLWLW) | Jared Bednar | Cale Makar, COL, D | Jon Cooper |
| 2020-21** | Tampa Bay Lightning** 4 | Montreal Canadians** 1 | (WWWLW) | Jon Cooper | Andrei Vasilevskiy, TB, G | Dominique Ducharme |
| 2019-20** | Tampa Bay Lightning** 4 | Dallas Stars 2 | (LWWWLW) | Jon Cooper | Victor Hedman, TB, D | Rick Bowness |
| 2018-19 | St. Louis Blues 4 | Boston Bruins 3 | (LWLWWLW) | Craig Berube | Ryan O'Reilly, STL, C | Bruce Cassidy |
| 2017-18 | Washington Capitals 4 | Vegas Golden Knights 1 | (LWWWW) | Barry Trotz | Alexander Ovechkin, WSH, LW | Gerard Gallant |
| 2016-17 | Pittsburgh Penguins 4 | Nashville Predators 2 | (WWLLWW) | Mike Sullivan | Sidney Crosby, PIT, C | Peter Laviolette |
| 2015-16 | Pittsburgh Penguins 4 | San Jose Sharks 2 | (WWLWLW) | Mike Sullivan | Sidney Crosby, PIT, C | Peter DeBoer |
| 2014-15 | Chicago Blackhawks 4 | Tampa Bay Lightning 2 | (WLLWWW) | Joel Quenneville | Duncan Keith, CHI, D | Jon Cooper |
| 2013-14 | Los Angeles Kings 4 | New York Rangers 1 | (WWWLW) | Darryl Sutter | Justin Williams, LA, RW | Alain Vigneault |
| 2012-13 | Chicago Blackhawks* 4 | Boston Bruins 2 | (WLLWWW) | Joel Quenneville | Patrick Kane, CHI, RW | Claude Julien |
| 2011-12 | Los Angeles Kings 4 | New Jersey Devils 2 | (WWWLLW) | Darryl Sutter | Jonathan Quick, LA, G | Peter DeBoer |
| 2010-11 | Boston Bruins 4 | Vancouver Canucks* 3 | (LLWWLWW) | Claude Julien | Tim Thomas, BOS, G | Alain Vigneault |
| 2009-10 | Chicago Blackhawks 4 | Philadelphia Flyers 2 | (WWLLWW) | Joel Quenneville | Jonathan Toews, CHI, C | Peter Laviolette |
| 2008-09 | Pittsburgh Penguins 4 | Detroit Red Wings 3 | (LLWWLWW) | Dan Bylsma | Evgeni Malkin, PIT, C | Mike Babcock |
| 2007-08 | Detroit Red Wings* 4 | Pittsburgh Penguins 2 | (WWLWLW) | Mike Babcock | Henrik Zetterberg, DET, LW | Michel Therrien |
| 2006-07 | Anaheim Mighty Ducks 4 | Ottawa Senators 1 | (WWLWW) | Randy Carlyle | Scott Niedermayer, ANA, D | Bryan Murray |
| 2005-06 | Carolina Hurricanes 4 | Edmonton Oilers 3 | (WWLWLLW) | Peter Laviolette | Cam Ward, CAR, G | Craig MacTavish |
| 2004-05 | SEASON NOT PLAYED | LOCKOUT | ||||
| 2003-04 | Tampa Bay Lightning 4 | Calgary Flames 3 | (LWLWLWW) | John Tortorella | Brad Richards, TB, C | Darryl Sutter |
| 2002-03 | New Jersey Devils 4 | Anaheim Mighty Ducks 3 | (WWLLWLW) | Pat Burns | Jean-Sebastien Giguere, ANA, G | Mike Babcock |
| 2001-02 | Detroit Red Wings 4 | Carolina Hurricanes 1 | (LWWWW) | Scotty Bowman | Nicklas Lidstrom, DET, D | Paul Maurice |
| 2000-01 | Colorado Avalanche 4 | New Jersey Devils 3 | (WLWLLWW) | Bob Hartley | Patrick Roy, COL, G | Larry Robinson |
| 1999-00 | New Jersey Devils 4 | Dallas Stars 2 | (WLWWLW) | Larry Robinson | Scott Stevens, NJ, D | Ken Hitchcock |
| 1998-99 | Dallas Stars 4 | Buffalo Sabres 2 | (LWWLWW) | Ken Hitchcock | Joe Nieuwendyk, DAL, C | Lindy Ruff |
| 1997-98 | Detroit Red Wings 4 | Washington Capitols 0 | (WWWW) | Scotty Bowman | Steve Yzerman, DET, C | Ron Wilson |
| 1996-97 | Detroit Red Wings 4 | Philadelphia Flyers 0 | (WWWW) | Scotty Bowman | Mike Vernon, DET, G | Terry Murray |
| 1995-96 | Colorado Avalanche* 4 | Florida Panthers 0 | (WWWW) | Marc Crawford | Joe Sakic, COL, C | Doug Maclean |
| 1994-95 | New Jersey Devils 4 | Detroit Red Wings* 0 | (WWWW) | Jacques Lemaire | Claude Lemieux, NJ, LW | Scotty Bowman |
| 1993-94 | New York Rangers 4 | Vancouver Canucks 3 | (LWWWLLW) | Mike Keenan | Brian Leetch, NYR, D | Pat Quinn |
| 1992-93 | Montreal Canadiens 4 | Los Angeles Kings 1 | (LWWWW) | Jacques Demers | Patrick Roy, MTL, G | Barry Melrose |
| 1991-92 | Pittsburgh Penguins* 4 | Chicago Blackhawks 0 | (WWWW) | Scotty Bowman | Mario Lemieux, PIT, C | Mike Keenan |
| 1990-91 | Pittsburgh Penguins 4 | Minnesota North Stars 2 | (LWLWWW) | Bob Johnson | Mario Lemieux, PIT, C | Bob Gainey |
| 1989-90 | Edmonton Oilers 4 | Boston Bruins 1 | (WWLWW) | John Muckler | Bill Ranford, EDM, G | Mike Milbury |
| 1988-89 | Calgary Flames 4 | Montreal Canadiens 2 | (WLLWWW) | Terry Crisp | Al MacInnis, CGY, D | Pat Burns |
| 1987-88 | Edmonton Oilers 4 | Boston Bruins 0 | (WWWW) | Glen Sather | Wayne Gretzky, EDM, C | Terry O'Reilly |
| 1986-87 | Edmonton Oilers 4 | Philadelphia Flyers 3 | (WWLWLLW) | Glen Sather | Ron Hextall, PHI, G | Mike Keenan |
| 1985-86 | Montreal Canadiens 4 | Calgary Flames 1 | (LWWWW) | Jean Perron | Patrick Roy, MTL, G | Bob Johnson |
| 1984-85 | Edmonton Oilers* 4 | Philadelphia Flyers 1 | (LWWWW) | Glen Sather | Wayne Gretzky, EDM, C | Mike Keenan |
| 1983-84 | Edmonton Oilers 4 | New York Islanders 1 | (WLWWW) | Glen Sather | Mark Messier, EDM, LW | Al Arbour |
| 1982-83 | New York Islanders 4 | Edmonton Oilers 0 | (WWWW) | Al Arbour | Billy Smith, NYI, G | Glen Sather |
| 1981-82 | New York Islanders 4 | Vancouver Canucks 0 | (WWWW) | Al Arbour | Mike Bossy, NYI, RW | Roger Neilson |
| 1980-81 | New York Islanders 4 | Minnesota North Stars 1 | (WWWLW) | Al Arbour | Butch Goring, NYI, C | Glen Sonmor |
| 1979-80 | New York Islanders 4 | Philadelphia Flyers 2 | (WLWWLW) | Al Arbour | Bryan Trottier, NYI, C | Pat Quinn |
| 1978-79 | Montreal Canadiens 4 | New York Rangers 1 | (LWWWW) | Scotty Bowman | Bob Gainey, MTL, LW | Fred Shero |
| 1977-78 | Montreal Canadiens 4 | Boston Bruins 2 | (WWLLWW) | Scotty Bowman | Larry Robinson, MTL, D | Don Cherry |
| 1976-77 | Montreal Canadiens 4 | Boston Bruins 0 | (WWWW) | Scotty Bowman | Guy Lafleur, MTL, RW | Don Cherry |
| 1975-76 | Montreal Canadiens 4 | Philadelphia Flyers 0 | (WWWW) | Scotty Bowman | Reggie Leach, PHI, RW | Fred Shero |
| 1974-75 | Philadelphia Flyers 4 | Buffalo Sabres 2 | (WWLLWW) | Fred Shero | Bernie Parent, PHI, G | Floyd Smith |
| 1973-74 | Philadelphia Flyers 4 | Boston Bruins 2 | (LWWWLW) | Fred Shero | Bernie Parent, PHI, G | A. 'Bep' Guidolin |
| 1972-73 | Montreal Canadiens 4 | Chicago Blackhawks 2 | (WWLWLW) | Scotty Bowman | Yvan Cournoyer, MTL, RW | Billy Reay |
| 1971-72 | Boston Bruins 4 | New York Rangers 2 | (WWLWLW) | Tom Johnson | Bobby Orr, BOS, D | Emile Francis |
| 1970-71 | Montreal Canadiens 4 | Chicago Blackhawks 3 | (LLWWLWW) | Al MacNeil | Ken Dryden, MTL, G | Billy Reay |
| 1969-70 | Boston Bruins 4 | St. Louis Blues 0 | (WWWW) | Harry Sinden | Bobby Orr, BOS, D | Scotty Bowman |
| 1968-69 | Montreal Canadiens 4 | St. Louis Blues 0 | (WWWW) | Claude Ruel | Serge Savard, MTL, D | Scotty Bowman |
| 1967-68 | Montreal Canadiens 4 | St. Louis Blues 0 | (WWWW) | Toe Blake | Glenn Hall, STL, G | Scotty Bowman |
| 1966-67 | Toronto Maple Leafs 4 | Montreal Canadiens 2 | (LWWLWW) | Bunch Imlach | Dave Keon, TOR, C | Hector 'Toe' Blake |
| 1965-66 | Montreal Canadiens 4 | Detroit Red Wings 2 | (LLWWWW) | Toe Blake | Roger Crozier, DET, G | Sid Abel |
| 1964-65 | Montreal Canadiens 4 | Chicago Blackhawks 3 | (WWLLWLW) | Toe Blake | Jean Beliveau, MTL, C | Billy Reay |
| 1963-64 | Toronto Maple Leafs 4 | Detroit Red Wings 3 | (WLLWLWW) | Punch Imlach | Sid Abel | |
| 1962-63 | Toronto Maple Leafs 4 | Detroit Red Wings 1 | (WWLWW) | Punch Imlach | Sid Abel | |
| 1961-62 | Toronto Maple Leafs 4 | Chicago Blackhawks 2 | (WWLLWW) | Punch Imlach | Rudy Pilous | |
| 1960-61 | Chicago Blackhawks 4 | Detroit Red Wings 2 | (WLWLWW) | Rudy Pilous | Sid Abel | |
| 1959-60 | Montreal Canadiens 4 | Toronto Maple Leafs 0 | (WWWW) | Toe Blake | G. 'Punch' Imlach | |
| 1958-59 | Montreal Canadiens 4 | Toronto Maple Leafs 1 | (WWLWW) | Toe Blake | G. 'Punch' Imlach | |
| 1957-58 | Montreal Canadiens 4 | Boston Bruins 2 | (WLWLWW) | Toe Blake | Milt Schmidt | |
| 1956-57 | Montreal Canadiens 4 | Boston Bruins 1 | (WWWLW) | Toe Blake | Milt Schmidt | |
| 1955-56 | Montreal Canadiens 4 | Detroit Red Wings 1 | (WWLWW) | Toe Blake | Jimmy Skinner | |
| 1954-55 | Detroit Red Wings 4 | Montreal Canadiens 3 | (WWLLWLW) | Jimmy Skiner | Dick Irvin | |
| 1953-54 | Detroit Red Wings 4 | Montreal Canadiens 3 | (WLWWLLW) | Tommy Ivan | Dick Irvin | |
| 1952-53 | Montreal Canadiens 4 | Boston Bruins 1 | (WLWWW) | Dick Irvin | Lynn Patrick | |
| 1951-52 | Detroit Red Wings 4 | Montreal Canadiens 0 | (WWWW) | Tommy Ivan | Dick Irvin | |
| 1950-51 | Toronto Maple Leafs 4 | Montreal Canadiens 1 | (WLWWW) | Joe Primeau | Dick Irvin | |
| 1949-50 | Detroit Red Wings 4 | New York Rangers 3 | (WLWLLWW) | Tommy Ivan | Lynn Patrick | |
| 1948-49 | Toronto Maple Leafs 4 | Detroit Red Wings 0 | (WWWW) | Hap Day | Tommy Ivan | |
| 1947-48 | Toronto Maple Leafs 4 | Detroit Red Wings 0 | (WWWW) | Hap Day | Tommy Ivan | |
| 1946-47 | Toronto Maple Leafs 4 | Montreal Canadiens 2 | (LWWWLW) | Hap Day | Dick Irvin | |
| 1945-46 | Montreal Canadiens 4 | Boston Bruins 1 | (WWWLW) | Dick Irvin | A. 'Dit 'Clapper | |
| 1944-45 | Toronto Maple Leafs 4 | Detroit Red Wings 3 | (WWWLLLW) | Hap Day | Jack Adams | |
| 1943-44 | Montreal Canadiens 4 | Chicago Blackhawks 0 | (WWWW) | Dick Irvin | Paul Thompson | |
| 1942-43 | Detroit Red Wings 4 | Boston Bruins 0 | (WWWW) | Jack Adams | Art Ross | |
| 1941-42 | Toronto Maple Leafs 4 | Detroit Red Wings 3 | (LLLWWWW) | Hap Day | Jack Adams | |
| 1940-41 | Boston Bruins 4 | Detroit Red Wings 0 | (WWWW) | Cooney Weiland | Ebbie Goodfellow | |
| 1939-40 | New York Rangers 4 | Toronto Maple Leafs 2 | (WWLLWW) | Frank Boucher | Dick Irvin | |
| 1938-39 | Boston Bruins 4 | Toronto Maple Leafs 1 | (WLWWW) | Art Ross | Dick Irvin | |
| 1937-38 | Chicago Blackhawks 3 | Toronto Maple Leafs 1 | (WLWW) | Bill Stewart | Dick Irvin | |
| 1936-37 | Detroit Red Wings 3 | New York Rangers 2 | (LWLWW) | Jack Adams | Lester Patrick | |
| 1935-36 | Detroit Red Wings 3 | Toronto Maple Leafs 1 | (WWLW) | Jack Adams | Dick Irvin | |
| 1934-35 | Montreal Maroons 3 | Toronto Maple Leafs 0 | (WWW) | Tommy Gorman | Dick Irvin | |
| 1933-34 | Chicago Blackhawks 3 | Detroit Red Wings 1 | (WWLW) | Tommy Gorman | Herbie Lewis | |
| 1932-33 | New York Rangers 3 | Toronto Maple Leafs 1 | (WWLW) | Lester Patrick | Dick Irvin | |
| 1931-32 | Toronto Maple Leafs 3 | New York Rangers 0 | (WW) | Dick Irvin | Lester Patrick | |
| 1930-31 | Montreal Canadiens 3 | Chicago Blackhawks 2 | (WLLWW) | Cecil Hart | Dick Irvin | |
| 1929-30 | Montreal Canadiens 2 | Boston Bruins 0 | (WW) | Cecil Hart | Art Ross | |
| 1928-29 | Boston Bruins 2 | New York Rangers 0 | (WW) | Cy Denneny | Lester Patrick | |
| 1927-28 | New York Rangers 3 | Montreal Maroons 2 | (LWLWW) | Lester Patrick | Eddie Gerard | |
| 1926-27 | Ottawa Senators 2 | Boston Bruins 0 | (TWTW) | Dave Gill | Art Ross | |
| 1925-26 | Montreal Maroons 3 | Victoria Cougars 1 | (WWLW) | Eddie Gerard | Lester Patrick | |
| 1924-25 | Victoria Cougars 3 | Montreal Canadiens 1 | (WWLW) | Lester Patrick | Leo Dandurand | |
| 1923-24 | Montreal Canadiens 2 | Calgary Tigers 0 | (WW) | Leo Dandurand | Eddie Oatman | |
| 1922-23 | Ottawa Senators 2 | Edmonton Eskimos 0 | (WW) | Pete Green | Ken McKenzine | |
| 1921-22 | Toronto St. Pats 3 | Vancouver Millionaires 2 | (LWLWW) | Eddie Powers | Lloyd Cook/Frank Patrick | |
| 1920-21 | Ottawa Senators 3 | Vancouver Millionaires 2 | (LWWLW) | Pete Green | Lloyd Cook/Frank Patrick | |
| 1919-20 | Ottawa Senators 3 | Seattle Metropolitans 2 | (WWLLW) | Pete Green | Pete Muldoon | |
| 1918-19 | Seattle Metropolitans (tie) | Montreal Canadiens (tie) | (SMSTM) | SERIES STOPPED | FLU PANDEMIC | |
| 1917-18 | Toronto Arenas 3 | Vancouver Millionaires 2 | (WLWLW) | Dick Carroll | Frank Patrick | |
| 1916-17 | Seattle Metropolitans 3 | Montreal Canadiens 1 | (LWWW) | Pete Muldoon | George Kennedy | |
| 1915-16 | Montreal Canadiens 3 | Portland Rosebuds 2 | (LWWLW) | Newsy Lalonde | Edward Savage | |
| 1914-15 | Vancouver Millionaires 3 | Ottawa Senators 0 | (WWW) | Frank Patrick | Frank Shaughnessy |
Note: The NHL was established in 1917. Prior to becoming the sole professional hockey league in 1927, the Stanley Cup was played between champions of the multiple pro hockey leagues: NHL/NHA, PCHA, WCHL/WHL.