Roy started his NHL career with the Montreal Canadiens, for whom he played from 1987 to 1995. He was then traded to the Colorado Avalanche, playing with them until his retirement in 2003. He won four Stanley Cups, two with each team (1986, 1993, 1996, 2001), capturing the Conn Smythe Trophy (playoff MVP) the first three times. In 1989, 1990, 1992 Roy won the Vezina Trophy (best goaltender). He won the Jennings Trophy (least goals allowed) in 1987, 1988, 1989 (all shared with Brian Hayward), 1992, and 2002. Among the many goaltending NHL records Roy holds are wins (551), games played (1029), playoff wins (151), and playoff games played (247). The Avalanche retired Roy's jersey, number 33, on October 28, 2003.