Milestones Records Most NHL playoff games played by a goaltender (247) (third-most playoff games of all players) Most NHL playoff wins by a goaltender (151) First NHL goaltender to play 1,000 NHL games (finished with 1,029 games, later passed by Martin Brodeur ) First NHL goaltender to win 500 games Most Conn Smythe Trophy wins – 3 Awards As a player Calder Cup – 1985 Stanley Cup – 1986 , 1993 (Montreal); 1996 , 2001 (Colorado)Conn Smythe Trophy – 1986 , 1993 , 2001 William M. Jennings Trophy – 1987 *, 1988 *, 1989 *, 1992 , 2002 Vezina Trophy – 1989, 1990 , 1992NHL All-Star Game – 1988 , 1990 , 1991 , 1992 , 1993 , 1994 , 1997 , 1998 , 2001 , 2002 , 2003 NHL first All-Star team – 1989, 1990, 1992, 2002NHL second All-Star team – 1988, 1991NHL All-Rookie Team – 1986Trico Goaltending Award – 1989, 1990The Colorado Avalanche retired Roy's number 33 jersey on October 28, 2003 The Montreal Canadiens retired Roy's number 33 jersey on November 22, 2008 * Shared with Brian Hayward
As a coach
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