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Year Winner Loser Series Conn Smythe Winner -------------------------------------------------------------------------------------- 1998 ----------------- ------------------- --- --------------- 1997 Detroit Red Wings Philadelphia Flyers 4-0 Mike Vernon 1996 Colorado Avalanche Florida Panthers 4-0 Joe Sakic 1995 New Jersey Devils Detroit Red Wings 4-0 Claude Lemieux 1994 New York Rangers Vancouver Canucks 4-3 Brian Leetch 1993 Montreal Canadiens Los Angeles Kings 4-1 Patrick Roy 1992 Pittsburgh Penguins Chicago Black Hawks 4-0 Mario Lemieux 1991 Pittsburgh Penguins Minnesota North Stars 4-2 Mario Lemieux 1990 Edmonton Oilers Boston Bruins 4-1 Bill Rantford 1989 Calgary Flames Montreal Canadiens 4-2 Al Macinnis 1988 Edmonton Oilers Boston Bruins 4-0 Wayne Gretzky 1987 Edmonton Oilers Philadelphia Flyers 4-3 Ron Hextall 1986 Montreal Canadiens Calgary Flames 4-1 Patrick Roy 1985 Edmonton Oilers Philadelphia Flyers 4-1 Wayne Gretzky 1984 Edmonton Oilers New York Islanders 4-1 Mark Messier 1983 New York Islanders Edmonton Oilers 4-0 Bill Smith 1982 New York Islanders Vancouver Canucks 4-0 Mike Bossey 1981 New York Islanders Minnesota North Stars 4-1 Butch Goring 1980 New York Islanders Philadelphia Flyers 4-2 Brian Trotier 1979 Montreal Canadiens New York Rangers 4-1 Bob Gainey 1978 Montreal Canadiens Boston Bruins 4-2 Larry Robinson 1977 Montreal Canadiens Boston Bruins 4-0 Guy Lafleur 1976 Montreal Canadiens Philadelphia Flyers 4-0 Reggie Leetch 1975 Philadelphia Flyers Buffalo Sabres 4-2 Bernie Parent 1974 Philadelphia Flyers Boston Bruins 4-2 Bernie Parent 1973 Montreal Canadiens Chicago Black Hawks 4-2 Yvan Cournoyer 1972 Boston Bruins New York Rangers 4-2 Bobby Orr 1971 Montreal Canadiens Chicago Black Hawks 4-3 Ken Dryden 1970 Boston Bruins St. Louis Blues 4-0 Bobby Orr 1969 Montreal Canadiens St. Louis Blues 4-0 Serge Savard 1968 Montreal Canadiens St. Louis Blues 4-0 Glen Hall 1967 Toronto Maple Leafs Montreal Canadiens 4-2 Kave Keon 1966 Montreal Canadiens Detroit Red Wings 4-2 Roger Crozier 1965 Montreal Canadiens Chicago Black Hawks 4-3 Jean Belevieu 1964 Toronto Maple Leafs Detroit Red Wings 4-3 1963 Toronto Maple Leafs Detroit Red Wings 4-1 1962 Toronto Maple Leafs Chicago Black Hawks 4-2 1961 Chicago Black Hawks Detroit Red Wings 4-2 1960 Montreal Canadiens Toronto Maple Leafs 4-0 1959 Montreal Canadiens Toronto Maple Leafs 4-1 1958 Montreal Canadiens Boston Bruins 4-2 1957 Montreal Canadiens Boston Bruins 4-1 1956 Montreal Canadiens Detroit Red Wings 4-1 1955 Detroit Red Wings Montreal Canadiens 4-3 1954 Detroit Red Wings Montreal Canadiens 4-3 1953 Montreal Canadiens Boston Bruins 4-1 1952 Detroit Red Wings Montreal Canadiens 4-0 1951 Toronto Maple Leafs Montreal Canadiens 4-1 1950 Detroit Red Wings New York Rangers 4-3 1949 Toronto Maple Leafs Detroit Red Wings 4-0 1948 Toronto Maple Leafs Detroit Red Wings 4-0 1947 Toronto Maple Leafs Montreal Canadiens 4-2 1946 Montreal Canadiens Boston Bruins 4-1 1945 Toronto Maple Leafs Detroit Red Wings 4-3 1944 Montreal Canadiens Chicago Black Hawks 4-0 1943 Detroit Red Wings Boston Bruins 4-0 1942 Toronto Maple Leafs Detroit Red Wings 4-3 1941 Boston Bruins Detroit Red Wings 4-0 1940 New York Rangers Toronto Maple Leafs 4-2 1939 Boston Bruins Toronto Maple Leafs 4-1