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The Conn Smythe Trophy is awarded to the most valuable player of the playoffs
| Season | Player | Team |
| 2000 | Scott Stevens | New Jersey Devils |
| 1999 | Joe Nieuwendyk | Dallas Stars |
| 1998 | Steve Yzerman | Detroit Red Wings |
| 1997 | Mike Vernon | Detroit Red Wings |
| 1996 | Joe Sakic | Colorado Avalanch |
| 1995 | Claude Lemieux | New Jersey Devils |
| 1994 | Brian Leetch | New York Rangers |
| 1993 | Patrick Roy | Montreal Canadiens |
| 1992 | Mario Lemieux | Pittsburgh Penguins |
| 1991 | Mario Lemieux | Pittsburgh Penguins |
| 1990 | Bill Ranford | Edmonton Oilers |
| 1989 | Al MacInnis | Calgary Flames |
| 1988 | Wayne Gretzky | Edmonton Oilers |
| 1987 | Ron Hextall | Philadelphia Flyers |
| 1986 | Patrick Roy | Montreal Canadiens |
| 1985 | Wayne Gretzky | Edmonton Oilers |
| 1984 | Mark Messier | Edmonton Oilers |
| 1983 | Billy Smith | New York Islanders |
| 1982 | Mike Bossy | New York Islanders |
| 1981 | Butch Goring | New York Islanders |
| 1980 | Bryan Trottier | New York Islanders |
| 1979 | Bob Gainey | Montreal Canadiens |
| 1978 | Larry Robinson | Montreal Canadiens |
| 1977 | Guy Lafluer | Montreal Canadiens |
| 1976 | Reggie Leach | Philadelphia Flyers |
| 1975 | Bernie Parent | Philadelphia Flyers |
| 1974 | Bernie Parent | Philadelphia Flyers |
| 1973 | Yvan Cournoyer | Montreal Canadiens |
| 1972 | Bobby Orr | Boston Bruins |
| 1971 | Ken Dryden | Montreal Canadiens |
| 1970 | Bobby Orr | Boston Bruins |
| 1969 | Serge Savard | Montreal Canadiens |
| 1968 | Glenn Hall | St. Louis Blues |
| 1967 | Dave Keon | Toronto Maple Leafs |
| 1966 | Roger Crozier | Detroit Red Wings |
| 1965 | Jean Beliveau | Montreal Canadiens |
