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May 23: On this day in 1968, the Leafs traded away another important component from their Stanley Cup winning years, sending right-winger Jim Pappin to Chicago for defenseman Pierre Pilote who had earned his Hall-of-Fame status after 13 solid seasons with the Black Hawks. Pilote played just one season, the final year of his career in 1968-69 as a Leaf. Meanwhile Pappin went on to play 7 productive seasons with Chicago where he scored 216 goals.
since the Leafs last Stanley Cup victory on May 02, 1967.
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On This Day In Leafs History
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The Holy Grail of Hockey - Stanley Cup Champions
| Year | Winner | Loser | Conn-Smythe Trophy | Series Victory | Winning Coach | Losing Coach |
| 2013 | Chicago Black Hawks 4 | Boston Bruins 2 | Patrick Kane | (WLLWWW) | Joel Quenneville | Claude Julien |
| 2012 | Los Angeles Kings 4 | New Jersey Devils 2 | Jonathan Quick | WWWLLW | Darryl Sutter | Pete Deboer |
| 2011 | Boston Bruins 4 | Vancouver Canucks 3 | Tim Thomas | LLWWLWW | Claude Julien | Alain Vigneault |
| 2010 | Chicago Blackhawks 4 | Philadelphia Flyers 2 | Jonathan Toews | (WWLLWW) | Joel Quenneville | Peter Laviolette |
| 2009 | Pittsburgh Penguins 4 | Detroit Red Wings 3 | Evgeni Malkin | (LLWWLWW) | Dan Bylsma | Mike Babcock |
| 2008 | Detroit Red Wings 4 | Pittsburgh Penguins 2 | Henrik Zetterberg | (WWLWLW) | Mike Babcock | Michel Therrien |
| 2007 | Anaheim Ducks 4 | Ottawa Senators 1 | Scott Niedermayer | (WWLWW) | Randy Carlyle | Bryan Murray |
| 2006 | Carolina Hurricanes 4 | Edmonton Oilers 3 | Cam Ward | (WWLWLLW) | Peter Laviolette | Craig MacTavish |
| 2005 | * No decision - NHL Strike | --- | --- | --- | --- | --- |
| 2004 | Tampa Bay Lightning 4 | Calgary Flames 3 | Brad Richards | (LWLWLWW) | John Tortorella | Darryl Sutter |
| 2003 | New Jersey Devils 4 | Anaheim Mighty Ducks 3 | Jean-Sebastien Giguere | (WWLLWLW) | Pat Burns | Mike Babcock |
| 2002 | Detroit Red Wings 4 | Carolina Hurricanes 1 | Nicklas Lidstrom | (LWWWW) | Scotty Bowman | Paul Maurice |
| 2001 | Colorado Avalanche 4 | New Jersey Devils 3 | Patrick Roy | (WLWLLWW) | Bob Hartley | Larry Robinson |
| 2000 | New Jersey Devils 4 | Dallas Stars 2 | Scott Stevens | (WLWWLW) | Larry Robinson | Ken Hitchcock |
| 1999 | Dallas Stars 4 | Buffalo Sabres 2 | Joe Nieuwendyk | (LWWLWW) | Ken Hitchcock | Lindy Ruff |
| 1998 | Detroit Red Wings 4 | Washington Capitols 0 | Steve Yzerman | (WWWW) | Scotty Bowman | Ron Wilson |
| 1997 | Detroit Red Wings 4 | Philadelphia Flyers 0 | Mike Vernon | (WWWW) | Scotty Bowman | Terry Murray |
| 1996 | Colorado Avalanche 4 | Florida Panthers 0 | Joe Sakic | (WWWW) | Marc Crawford | Doug Maclean |
| 1995 | New Jersey Devils 4 | Detroit Red Wings 0 | Claude Lemieux | (WWWW) | Jacques Lemaire | Scotty Bowman |
| 1994 | New York Rangers 4 | Vancouver Canucks 3 | Brian Leetch | (LWWWLLW) | Mike Keenan | Pat Quinn |
| 1993 | Montreal Canadiens 4 | Los Angeles Kings 1 | Patrick Roy | (LWWWW) | Jacques Demers | Barry Melrose |
| 1992 | Pittsburgh Penguins 4 | Chicago Blackhawks 0 | Mario Lemieux | (WWWW) | Scotty Bowman | Mike Keenan |
| 1991 | Pittsburgh Penguins 4 | Minnesota North Stars 2 | Mario Lemieux | (LWLWWW) | Bob Johnson | Bob Gainey |
| 1990 | Edmonton Oilers 4 | Boston Bruins 1 | Bill Ranford | (WWLWW) | John Muckler | Mike Milbury |
| 1989 | Calgary Flames 4 | Montreal Canadiens 2 | Al MacInnis | (WLLWWW) | Terry Crisp | Pat Burns |
| 1988 | Edmonton Oilers 4 | Boston Bruins 0 | Wayne Gretzky | (WWWW) | Glen Sather | Terry O'Reilly |
| 1987 | Edmonton Oilers 4 | Philadelphia Flyers 3 | Ron Hextall | (WWLWLLW) | Glen Sather | Mike Keenan |
| 1986 | Montreal Canadiens 4 | Calgary Flames 1 | Patrick Roy | (LWWWW) | Jean Perron | Bob Johnson |
| 1985 | Edmonton Oilers 4 | Philadelphia Flyers 1 | Wayne Gretzky | (LWWWW) | Glen Sather | Mike Keenan |
| 1984 | Edmonton Oilers 4 | New York Islanders 1 | Mark Messier | (WLWWW) | Glen Sather | Al Arbour |
| 1983 | New York Islanders 4 | Edmonton Oilers 0 | Billy Smith | (WWWW) | Al Arbour | Glen Sather |
| 1982 | New York Islanders 4 | Vancouver Canucks 0 | Mike Bossy | (WWWW) | Al Arbour | Roger Neilson |
| 1981 | New York Islanders 4 | Minnesota North Stars 1 | Butch Goring | (WWWLW) | Al Arbour | Glen Sonmor |
| 1980 | New York Islanders 4 | Philadelphia Flyers 2 | Bryan Trottier | (WLWWLW) | Al Arbour | Pat Quinn |
| 1979 | Montreal Canadiens 4 | New York Rangers 1 | Bob Gainey | (LWWWW) | Scotty Bowman | Fred Shero |
| 1978 | Montreal Canadiens 4 | Boston Bruins 2 | Larry Robinson | (WWLLWW) | Scotty Bowman | Don Cherry |
| 1977 | Montreal Canadiens 4 | Boston Bruins 0 | Guy Lafleur | (WWWW) | Scotty Bowman | Don Cherry |
| 1976 | Montreal Canadiens 4 | Philadelphia Flyers 0 | Reggie Leach | (WWWW) | Scotty Bowman | Fred Shero |
| 1975 | Philadelphia Flyers 4 | Buffalo Sabres 2 | Bernie Parent | (WWLLWW) | Fred Shero | Floyd Smith |
| 1974 | Philadelphia Flyers 4 | Boston Bruins 2 | Bernie Parent | (LWWWLW) | Fred Shero | A. 'Bep' Guidolin |
| 1973 | Montreal Canadiens 4 | Chicago Blackhawks 2 | Yvan Cournoyer | (WWLWLW) | Scotty Bowman | Billy Reay |
| 1972 | Boston Bruins 4 | New York Rangers 2 | Bobby Orr | (WWLWLW) | Tom Johnson | Emile Francis |
| 1971 | Montreal Canadiens 4 | Chicago Blackhawks 3 | Ken Dryden | (LLWWLWW) | Al MacNeil | Billy Reay |
| 1970 | Boston Bruins 4 | St. Louis Blues 0 | Bobby Orr | (WWWW) | Harry Sinden | Scotty Bowman |
| 1969 | Montreal Canadiens 4 | St. Louis Blues 0 | Serge Savard | (WWWW) | Claude Ruel | Scotty Bowman |
| 1968 | Montreal Canadiens 4 | St. Louis Blues 0 | Glenn Hall | (WWWW) | Toe Blake | Scotty Bowman |
| 1967 | Toronto Maple Leafs 4 | Montreal Canadiens 2 | Dave Keon | (LWWLWW) | Bunch Imlach | Hector 'Toe' Blake |
| 1966 | Montreal Canadiens 4 | Detroit Red Wings 2 | Roger Crozier | (LLWWWW) | Toe Blake | Sid Abel |
| 1965 | Montreal Canadiens 4 | Chicago Blackhawks 3 | Jean Beliveau (Inaugural) | (WWLLWLW) | Toe Blake | Billy Reay |
| 1964 | Toronto Maple Leafs 4 | Detroit Red Wings 3 | (WLLWLWW) | Punch Imlach | Sid Abel | |
| 1963 | Toronto Maple Leafs 4 | Detroit Red Wings 1 | (WWLWW) | Punch Imlach | Sid Abel | |
| 1962 | Toronto Maple Leafs 4 | Chicago Blackhawks 2 | (WWLLWW) | Punch Imlach | Rudy Pilous | |
| 1961 | Chicago Blackhawks 4 | Detroit Red Wings 2 | (WLWLWW) | Rudy Pilous | Sid Abel | |
| 1960 | Montreal Canadiens 4 | Toronto Maple Leafs 0 | (WWWW) | Toe Blake | G. 'Punch' Imlach | |
| 1959 | Montreal Canadiens 4 | Toronto Maple Leafs 1 | (WWLWW) | Toe Blake | G. 'Punch' Imlach | |
| 1958 | Montreal Canadiens 4 | Boston Bruins 2 | (WLWLWW) | Toe Blake | Milt Schmidt | |
| 1957 | Montreal Canadiens 4 | Boston Bruins 1 | (WWWLW) | Toe Blake | Milt Schmidt | |
| 1956 | Montreal Canadiens 4 | Detroit Red Wings 1 | (WWLWW) | Toe Blake | Jimmy Skinner | |
| 1955 | Detroit Red Wings 4 | Montreal Canadiens 3 | (WWLLWLW) | Jimmy Skiner | Dick Irvin | |
| 1954 | Detroit Red Wings 4 | Montreal Canadiens 3 | (WLWWLLW) | Tommy Ivan | Dick Irvin | |
| 1953 | Montreal Canadiens 4 | Boston Bruins 1 | (WLWWW) | Dick Irvin | Lynn Patrick | |
| 1952 | Detroit Red Wings 4 | Montreal Canadiens 0 | (WWWW) | Tommy Ivan | Dick Irvin | |
| 1951 | Toronto Maple Leafs 4 | Montreal Canadiens 1 | (WLWWW) | Joe Primeau | Dick Irvin | |
| 1950 | Detroit Red Wings 4 | New York Rangers 3 | (WLWLLWW) | Tommy Ivan | Lynn Patrick | |
| 1949 | Toronto Maple Leafs 4 | Detroit Red Wings 0 | (WWWW) | Hap Day | Tommy Ivan | |
| 1948 | Toronto Maple Leafs 4 | Detroit Red Wings 0 | (WWWW) | Hap Day | Tommy Ivan | |
| 1947 | Toronto Maple Leafs 4 | Montreal Canadiens 2 | (LWWWLW) | Hap Day | Dick Irvin | |
| 1946 | Montreal Canadiens 4 | Boston Bruins 1 | (WWWLW) | Dick Irvin | A. 'Dit 'Clapper | |
| 1945 | Toronto Maple Leafs 4 | Detroit Red Wings 3 | (WWWLLLW) | Hap Day | Jack Adams | |
| 1944 | Montreal Canadiens 4 | Chicago Blackhawks 0 | (WWWW) | Dick Irvin | Paul Thompson | |
| 1943 | Detroit Red Wings 4 | Boston Bruins 0 | (WWWW) | Jack Adams | Art Ross | |
| 1942 | Toronto Maple Leafs 4 | Detroit Red Wings 3 | (LLLWWWW) | Hap Day | Jack Adams | |
| 1941 | Boston Bruins 4 | Detroit Red Wings 0 | (WWWW) | Cooney Weiland | Ebbie Goodfellow | |
| 1940 | New York Rangers 4 | Toronto Maple Leafs 2 | (WWLLWW) | Frank Boucher | Dick Irvin | |
| 1939 | Boston Bruins 4 | Toronto Maple Leafs 1 | (WLWWW) | Art Ross | Dick Irvin | |
| 1938 | Chicago Blackhawks 3 | Toronto Maple Leafs 1 | (WLWW) | Bill Stewart | Dick Irvin | |
| 1937 | Detroit Red Wings 3 | New York Rangers 2 | (LWLWW) | Jack Adams | Lester Patrick | |
| 1936 | Detroit Red Wings 3 | Toronto Maple Leafs 1 | (WWLW) | Jack Adams | Dick Irvin | |
| 1935 | Montreal Maroons 3 | Toronto Maple Leafs 0 | (WWW) | Tommy Gorman | Dick Irvin | |
| 1934 | Chicago Blackhawks 3 | Detroit Red Wings 1 | (WWLW) | Tommy Gorman | Herbie Lewis | |
| 1933 | New York Rangers 3 | Toronto Maple Leafs 1 | (WWLW) | Lester Patrick | Dick Irvin | |
| 1932 | Toronto Maple Leafs 3 | New York Rangers 0 | (WW) | Dick Irvin | Lester Patrick | |
| 1931 | Montreal Canadiens 3 | Chicago Blackhawks 2 | (WLLWW) | Cecil Hart | Dick Irvin | |
| 1930 | Montreal Canadiens 2 | Boston Bruins 0 | (WW) | Cecil Hart | Art Ross | |
| 1929 | Boston Bruins 2 | New York Rangers 0 | (WW) | Cy Denneny | Lester Patrick | |
| 1928 | New York Rangers 3 | Montreal Maroons 2 | (LWLWW) | Lester Patrick | Eddie Gerard | |
| 1927 | Ottawa Senators 2 | Boston Bruins 0 | (TWTW) | Dave Gill | Art Ross | |
| 1926 | Montreal Maroons 3 | Victoria Cougars 1 | (WWLW) | Eddie Gerard | Lester Patrick | |
| 1925 | Victoria Cougars 3 | Montreal Canadiens 1 | (WWLW) | Lester Patrick | Leo Dandurand | |
| 1924 | Montreal Canadiens 2 | Calgary Tigers 0 | (WW) | Leo Dandurand | Eddie Oatman | |
| 1923 | Ottawa Senators 2 | Edmonton Eskimos 0 | (WW) | Pete Green | Ken McKenzine | |
| 1922 | Toronto St. Pats 3 | Vancouver Millionaires 2 | (LWLWW) | Eddie Powers | Lloyd Cook/Frank Patrick | |
| 1921 | Ottawa Senators 3 | Vancouver Millionaires 2 | (LWWLW) | Pete Green | Lloyd Cook/Frank Patrick | |
| 1920 | Ottawa Senators 3 | Seattle Metropolitans 2 | (WWLLW) | Pete Green | Pete Muldoon | |
| 1919 | **Incomplete - Flu Epidemic | Seattle 2 | Montreal 2 | (WLW - T - L) | Pete Muldoon (S) | Newsy Lalonde (M) |
| 1918 | Toronto Arenas 3 | Vancouver Millionaires 2 | (WLWLW) | Dick Carroll | Frank Patrick |
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* In 2005 the Stanley Cup will not be awarded because the players and owners, the NHL and NHLPA, Bob Goodenow and Gary Bettman, could not come to an agreement when splitting an estimated $2.1 billion in revenue. ** The first Stanley Cup to go unawarded in 112 years was a somber reaction to the 1919 influenza pandemic that killed over 20 million people worldwide. The series halted because of this epidemic which killed players including the death of Joe Hall of Montreal Canadiens. Five games had been completed when the series was stopped, each team having won two and tied one. Technically, the Seattle Metropolitans of the Pacific Coast Hockey Association could have taken the cup after most of the Montreal Canadiens team of the National Hockey League fell ill. Seattle declined to take the championship under those circumstances. The results are shown below: |
Mar. 19, at Seattle - Seattle 7, Montreal 0; Mar. 22, at Seattle - Montreal 4, Seattle 2; | Mar. 24, at Seattle - Seattle 7, Montreal 2; Mar. 26, at Seattle - Montreal 0, Seattle 0; | Mar. 30, at Seattle - Montreal 4, Seattle 3. |
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