| Año | Equipo ganador | Entrenador | Juegos | Equipo perdedor | Entrenador | Objetivo ganador |
| 1927 | Senadores de Ottawa (C) (5, 4-1) | Dave Gill | 2-0-2 | Boston Bruins (A) (1, 0-1) | Art Ross | Cy Denneny (7:30, segundo) |
| 1928 | New York Rangers (A) (1, 1-0) | Lester Patrick-playing | 3-2 | Cimarrones de Montreal (C) (2, 1-1) | Eddie Gerard | Frank Boucher (3:35, tercero) |
| 1929 | Boston Bruins (A) (2, 1-1) | Art Ross | 2-0 | New York Rangers (A) (2, 1-1) | Lester Patrick | Bill Carson (18:02, tercero) |
| 1930 | Montreal Canadiens (C) (6, 3-2) | Cecil Hart | 2-0 | Boston Bruins (A) (3, 1-2) | Art Ross | Howie Morenz (1:00, segundo) |
| 1931 | Montreal Canadiens (C) (7, 4-2) | 3-2 | Chicago Black Hawks (A) (1, 0-1) | Dick Irvin | Johnny Gagnon (9:59, segundo) |
| 1932 | Toronto Maple Leafs (C) (3, 3-0) | Dick Irvin | 3-0 | New York Rangers (A) (3, 1-2) | Lester Patrick | Ace Bailey (15:07, tercero) |
| 1933 | New York Rangers (A) (4, 2-2) | Lester Patrick | 3-1 | Toronto Maple Leafs (C) (4, 3-1) | Dick Irvin | Bill Cook (7:34, OT) |
| 1934 | Chicago Black Hawks (A) (2, 1-1) | Tommy Gorman | 3-1 | Detroit Red Wings (A) (1, 0-1) | Jack Adams | Mush March (10:05, segunda OT) |
| 1935 | Cimarrones de Montreal (C) (2, 2-1) | 3-0 | Toronto Maple Leafs (C) (5, 3-2) | Dick Irvin | Baldy Northcott (16:18, segundo) |
| 1936 | Detroit Red Wings (A) (2, 1-1) | Jack Adams | 3-1 | Toronto Maple Leafs (C) (6, 3-3) | Pete Kelly (9:45, tercero) |
| 1937 | Detroit Red Wings (A) (3, 2-1) | 3-2 | New York Rangers (A) (5, 2-3) | Lester Patrick | Marty Barry (19:22, primero) |
| 1938 | Chicago Black Hawks (A) (3, 2-1) | Bill Stewart | 3-1 | Toronto Maple Leafs (C) (7, 3-4) | Dick Irvin | Carl Voss (16:45, segundo) |
| 1939 | Boston Bruins (4, 2-2) | Art Ross | 4-1 | Toronto Maple Leafs (8, 3-5) | Roy Conacher (17:54, segundo) |
| 1940 | New York Rangers (6, 3-3) | Frank Boucher | 4-2 | Toronto Maple Leafs (9, 3-6) | Bryan Hextall (2:07, OT) |
| 1941 | Boston Bruins (5, 3-2) | Cooney Weiland | 4-0 | Detroit Red Wings (4, 2-2) | Jack Adams | Bobby Bauer (8:43, segundo) |
| 1942 | Toronto Maple Leafs (10, 4-6) | Hap Day | 4-3 | Detroit Red Wings (5, 2-3) | Jack Adams | Pete Langelle (9:48, tercero) |
| 1943 | Detroit Red Wings (6, 3-3) | Jack Adams | 4-0 | Boston Bruins (6, 3-3) | Art Ross | Joe Carveth (12:09, primero) |
| 1944 | Montreal Canadiens (8, 5-2) | Dick Irvin | 4-0 | Chicago Black Hawks (4, 2-2) | Paul Thompson | Toe Blake (9:12, OT) |
| 1945 | Toronto Maple Leafs (11, 5-6) | Hap Day | 4-3 | Detroit Red Wings (7, 3-4) | Jack Adams | Babe Pratt (12:14, tercera) |
| 1946 | Montreal Canadiens (9, 6-2) | Dick Irvin | 4-1 | Boston Bruins (7, 3-4) | Dit Clapper | Toe Blake (11:06, tercero) |
| 1947 | Toronto Maple Leafs (12, 6-6) | Hap Day | 4-2 | Montreal Canadiens (10, 6-3) | Dick Irvin | Ted Kennedy (14:39, tercero) |
| 1948 | Toronto Maple Leafs (13, 7-6) | 4-0 | Detroit Red Wings (8, 3-5) | Tommy Ivan | Harry Watson (11:13, primero) |
| 1949 | Toronto Maple Leafs (14, 8-6) | 4-0 | Detroit Red Wings (9, 3-6) | Cal Gardner (19:45, segundo) |
| 1950 | Detroit Red Wings (10, 4-6) | Tommy Ivan | 4-3 | New York Rangers (7, 3-4) | Lynn Patrick | Pete Babando (8:31, segundo tiempo extra) |
| 1951 | Toronto Maple Leafs (15, 9-6) | Joe Primeau | 4-1 | Montreal Canadiens (11, 6-4) | Dick Irvin | Bill Barilko (2:53, OT) |
| 1952 | Detroit Red Wings (11, 5-6) | Tommy Ivan | 4-0 | Montreal Canadiens (12, 6-5) | Metro Prystai (6:50, primero) |
| 1953 | Montreal Canadiens (13, 7-5) | Dick Irvin | 4-1 | Boston Bruins (8, 3-5) | Lynn Patrick | Elmer Lach (1:22, OT) |
| 1954 | Detroit Red Wings (12, 6-6) | Tommy Ivan | 4-3 | Montreal Canadiens (14, 7-6) | Dick Irvin | Tony Leswick (4:20, OT) |
| 1955 | Detroit Red Wings (13, 7-6) | Jimmy Skinner | 4-3 | Montreal Canadiens (15, 7-7) | Gordie Howe (19:49, segundo) |
| 1956 | Montreal Canadiens (16, 8-7) | Toe Blake | 4-1 | Detroit Red Wings (14, 7-7) | Jimmy Skinner | Maurice Richard (15:08, segundo) |
| 1957 | Montreal Canadiens (17, 9-7) | 4-1 | Boston Bruins (9, 3-6) | Milt Schmidt | Dickie Moore (0:14, segundo) |
| 1958 | Montreal Canadiens (18, 10-7) | 4-2 | Boston Bruins (10, 3-7) | Bernie Geoffrion (19:26, segundo) |
| 1959 | Montreal Canadiens (19, 11-7) | 4-1 | Toronto Maple Leafs (16, 9-7) | Punch Imlach | Marcel Bonin (9:55, segundo) |
| 1960 | Montreal Canadiens (20, 12-7) | 4-0 | Toronto Maple Leafs (17, 9-8) | Jean Beliveau (8:16, primero) |
| 1961 | Chicago Black Hawks (5, 3-2) | Rudy Pilous | 4-2 | Detroit Red Wings (15, 7-8) | Sid Abel | Ab McDonald (18:49, segundo) |
| 1962 | Toronto Maple Leafs (18, 10-8) | Punch Imlach | 4-2 | Halcones Negros de Chicago (6, 3-3) | Rudy Pilous | Dick Duff (14:14, tercero) |
| 1963 | Toronto Maple Leafs (19, 11-8) | 4-1 | Detroit Red Wings (16, 7-9) | Sid Abel | Eddie Shack (13:28, tercero) |
| 1964 | Toronto Maple Leafs (20, 12-8) | 4-3 | Detroit Red Wings (17, 7-10) | Andy Bathgate (3:04, primero) |
| 1965 | Montreal Canadiens (21, 13-7) | Toe Blake | 4-3 | Chicago Black Hawks (7, 3-4) | Billy Reay | Jean Beliveau (0:14, primero) |
| 1966 | Montreal Canadiens (22, 14-7) | 4-2 | Detroit Red Wings (18, 7-11) | Sid Abel | Henri Richard (2:20, OT) |
| 1967 | Toronto Maple Leafs (21, 13-8) | Punch Imlach | 4-2 | Montreal Canadiens (23, 14-8) | Toe Blake | Jim Pappin (19:24, segundo) |
| 1968 | Montreal Canadiens (E) (24, 15-8) | Toe Blake | 4-0 | St. Louis Blues (W) (1, 0-1) | Scotty Bowman | J. C. Tremblay (11:40, tercero) |
| 1969 | Montreal Canadiens (E) (25, 16-8) | Claude Ruel | 4-0 | St. Louis Blues (W) (2, 0-2) | John Ferguson (3:02, tercero) |
| 1970 | Boston Bruins (E) (11, 4-7) | Harry Sinden | 4-0 | St. Louis Blues (W) (3, 0-3) | Bobby Orr (0:40, OT) |
| 1971 | Montreal Canadiens (E) (26, 17-8) | Al MacNeil | 4-3 | Chicago Black Hawks (W) (8, 3-5) | Billy Reay | Henri Richard (2:34, tercero) |
| 1972 | Boston Bruins (E) (12, 5-7) | Tom Johnson | 4-2 | New York Rangers (E) (8, 3-5) | Emile Francis | Bobby Orr (11:18, primero) |
| 1973 | Montreal Canadiens (E) (27, 18-8) | Scotty Bowman | 4-2 | Chicago Black Hawks (W) (9, 3-6) | Billy Reay | Yvan Cournoyer (8:13, tercero) |
| 1974 | Philadelphia Flyers (W) (1, 1-0) | Fred Shero | 4-2 | Boston Bruins (E) (13, 5-8) | Bep Guidolin | Rick MacLeish (14:48, primero) |
| 1975 | Philadelphia Flyers (CC) (2, 2-0) | 4-2 | Buffalo Sabres (PW) (1, 0-1) | Floyd Smith | Bob Kelly (0:11, tercero) |
| 1976 | Montreal Canadiens (PW) (28, 19-8) | Scotty Bowman | 4-0 | Philadelphia Flyers (CC) (3, 2-1) | Fred Shero | Guy Lafleur (14:18, tercero) |
| 1977 | Montreal Canadiens (PW) (29, 20-8) | 4-0 | Boston Bruins (PW) (14, 5-9) | Don Cherry | Jacques Lemaire (4:32, OT) |
| 1978 | Montreal Canadiens (PW) (30, 21-8) | 4-2 | Boston Bruins (PW) (15, 5-10) | Mario Tremblay (9:20, primero) |
| 1979 | Montreal Canadiens (PW) (31, 22-8) | 4-1 | New York Rangers (CC) (9, 3-6) | Fred Shero | Jacques Lemaire (1:02, segundo) |
| 1980 | New York Islanders (CC) (1, 1-0) | Al Arbour | 4-2 | Philadelphia Flyers (CC) (4, 2-2) | Pat Quinn | Bob Nystrom (7:11, OT) |
| 1981 | New York Islanders (CC) (2, 2-0) | 4-1 | Minnesota North Stars (PW) (1, 0-1) | Glen Sonmor | Wayne Merrick (5:37, primero) |
| 1982 | New York Islanders (PW) (3, 3-0) | 4-0 | Vancouver Canucks (CC) (1, 0-1) | Roger Neilson | Mike Bossy (5:00, segundo) |
| 1983 | New York Islanders (PW) (4, 4-0) | 4-0 | Edmonton Oilers (CC) (1, 0-1) | Glen Sather | Mike Bossy (12:39, primero) |
| 1984 | Edmonton Oilers (CC) (2, 1-1) | Glen Sather | 4-1 | New York Islanders (PW) (5, 4-1) | Al Arbour | Ken Linseman (0:38, segundo) |
| 1985 | Edmonton Oilers (CC) (3, 2-1) | 4-1 | Philadelphia Flyers (PW) (5, 2-3) | Mike Keenan | Paul Coffey (17:57, primero) |
| 1986 | Montreal Canadiens (PW) (32, 23-8) | Jean Perron | 4-1 | Calgary Flames (CC) (1, 0-1) | Bob Johnson | Bobby Smith (10:30, tercero) |
| 1987 | Edmonton Oilers (CC) (4, 3-1) | Glen Sather | 4-3 | Philadelphia Flyers (PW) (6, 2-4) | Mike Keenan | Jari Kurri (14:59, segundo) |
| 1988 | Edmonton Oilers (CC) (5, 4-1) | 4-0 | Boston Bruins (PW) (16, 5-11) | Terry O'Reilly | Wayne Gretzky (9:44, segundo) |
| 1989 | Calgary Flames (CC) (2, 1-1) | Terry Crisp | 4-2 | Montreal Canadiens (PW) (33, 23-9) | Pat Burns | Doug Gilmour (11:02, tercero) |
| 1990 | Edmonton Oilers (CC) (6, 5-1) | John Muckler | 4-1 | Boston Bruins (PW) (17, 5-12) | Mike Milbury | Craig Simpson (9:31, segundo) |
| 1991 | Pingüinos de Pittsburgh (PW) (1, 1-0) | Bob Johnson | 4-2 | Minnesota North Stars (CC) (2, 0-2) | Bob Gainey | Ulf Samuelsson (2:00, primero) |
| 1992 | Pingüinos de Pittsburgh (PW) (2, 2-0) | Scotty Bowman | 4-0 | Chicago Blackhawks (CC) (10, 3-7) | Mike Keenan | Ron Francis (7:59, tercero) |
| 1993 | Montreal Canadiens (PW) (34, 24-9) | Jacques Demers | 4-1 | Los Ángeles Kings (CC) (1, 0-1) | Barry Melrose | Kirk Muller (3:51, segundo) |
| 1994 | New York Rangers (CE) (10, 4-6) | Mike Keenan | 4-3 | Vancouver Canucks (WC) (2, 0-2) | Pat Quinn | Mark Messier (13:29, segundo) |
| 1995 | New Jersey Devils (EC) (1, 1-0) | Jacques Lemaire | 4-0 | Detroit Red Wings (WC) (19, 7-12) | Scotty Bowman | Neal Broten (7:56, segundo) |
| 1996 | Colorado Avalanche (WC) (1, 1-0) | Marc Crawford | 4-0 | Panteras de Florida (CE) (1, 0-1) | Doug MacLean | Uwe Krupp (4:31, tercer tiempo extra) |
| 1997 | Detroit Red Wings (WC) (20, 8-12) | Scotty Bowman | 4-0 | Philadelphia Flyers (EC) (7, 2-5) | Terry Murray | Darren McCarty (13:02, segundo) |
| 1998 | Detroit Red Wings (WC) (21, 9-12) | 4-0 | Washington Capitals (EC) (1, 0-1) | Ron Wilson | Martin Lapointe (2:26, segundo) |
| 1999 | Dallas Stars (WC) (3, 1-2) | Ken Hitchcock | 4-2 | Buffalo Sabres (CE) (2, 0-2) | Lindy Ruff | Brett Hull (14:51, tercera OT) |
| 2000 | New Jersey Devils (CE) (2, 2-0) | Larry Robinson (interino) | 4-2 | Dallas Stars (WC) (4, 1-3) | Ken Hitchcock | Jason Arnott (8:20, segundo tiempo extra) |
| 2001 | Colorado Avalanche (WC) (2, 2-0) | Bob Hartley | 4-3 | New Jersey Devils (CE) (3, 2-1) | Larry Robinson | Alex Tanguay (4:57, segundo) |
| 2002 | Detroit Red Wings (WC) (22, 10-12) | Scotty Bowman | 4-1 | Huracanes de Carolina (CE) (1, 0-1) | Paul Maurice | Brendan Shanahan (14:04, segundo) |
| 2003 | New Jersey Devils (EC) (4, 3-1) | Pat Burns | 4-3 | Mighty Ducks de Anaheim (WC) (1, 0-1) | Mike Babcock | Michael Rupp (2:22, segundo) |
| 2004 | Tampa Bay Lightning (CE) (1, 1-0) | John Tortorella | 4-3 | Calgary Flames (WC) (3, 1-2) | Darryl Sutter | Ruslan Fedotenko (14:38, segundo) |
| 2005 | Temporada cancelada debido al cierre patronal de la NHL 2004-05 |
| 2006 | Huracanes de Carolina (CE) (2, 1-1) | Peter Laviolette | 4-3 | Edmonton Oilers (WC) (7, 5-2) | Craig MacTavish | Frantisek Kaberle (4:18, segundo) |
| 2007 | Anaheim Ducks (WC) (2, 1-1) | Randy Carlyle | 4-1 | Senadores de Ottawa (CE) (1, 0-1) | Bryan Murray | Travis Moen (15:44, segundo) |
| 2008 | Detroit Red Wings (WC) (23, 11-12) | Mike Babcock | 4-2 | Pingüinos de Pittsburgh (CE) (3, 2-1) | Michel Therrien | Henrik Zetterberg (7:36, tercero) |
| 2009 | Pingüinos de Pittsburgh (CE) (4, 3-1) | Dan Bylsma | 4-3 | Detroit Red Wings (WC) (24, 11-13) | Mike Babcock | Maxime Talbot (10:07, segundo) |
| 2010 | Chicago Blackhawks (WC) (11, 4-7) | Joel Quenneville | 4-2 | Philadelphia Flyers (EC) (8, 2-6) | Peter Laviolette | Patrick Kane (4:06, OT) |
| 2011 | Boston Bruins (CE) (18, 6-12) | Claude Julien | 4-3 | Vancouver Canucks (WC) (3, 0-3) | Alain Vigneault | Patrice Bergeron (14:37, primero) |
| 2012 | Los Angeles Kings (WC) (2, 1-1) | Darryl Sutter | 4-2 | New Jersey Devils (EC) (5, 3-2) | Peter DeBoer | Jeff Carter (12:45, primero) |
| 2013 | Chicago Blackhawks (WC) (12, 5-7) | Joel Quenneville | 4-2 | Boston Bruins (CE) (19, 6-13) | Claude Julien | Dave Bolland (19:01, tercero) |
| 2014 | Los Angeles Kings (WC) (3, 2-1) | Darryl Sutter | 4-1 | New York Rangers (CE) (11, 4-7) | Alain Vigneault | Alec Martínez (14:43, segundo tiempo extra) |
| 2015 | Chicago Blackhawks (WC) (13, 6-7) | Joel Quenneville | 4-2 | Tampa Bay Lightning (CE) (2, 1-1) | Jon Cooper | Duncan Keith (17:13, segundo) |
| 2016 | Pingüinos de Pittsburgh (CE) (5, 4-1) | Mike Sullivan | 4-2 | San Jose Sharks (WC) (1, 0-1) | Peter DeBoer | Kris Letang (7:46, segundo) |
| 2017 | Pingüinos de Pittsburgh (CE) (6, 5-1) | 4-2 | Nashville Predators (WC) (1, 0-1) | Peter Laviolette | Patric Hornqvist (18:25, tercero) |
| 2018 | Washington Capitals (CE) (2, 1-1) | Barry Trotz | 4-1 | Vegas Golden Knights (WC) (1, 0-1) | Gerard Gallant | Lars Eller (12:23, tercero) |
| 2019 | St. Louis Blues (WC) (4, 1-3) | Craig Berube (interino) | 4-3 | Boston Bruins (CE) (20, 6-14) | Bruce Cassidy | Alex Pietrangelo (19:52, primero) |
| 2020 | Tampa Bay Lightning (CE) (3, 2-1) | Jon Cooper | 4-2 | Dallas Stars (WC) (5, 1-4) | Rick Bowness (interino) | Brayden Point (12:23, primero) |
| 2021 | Tampa Bay Lightning (4, 3-1) | 4-1 | Montreal Canadiens (35, 24-10) | Dominique Ducharme (interino) | Ross Colton (13:27, segundo) |
| 2022 | Avalancha de Colorado | | 4-2 | Rayo de Tampa Bay | | |
