Fleury was drafted by the Calgary Flames with the 166th overall pick in the 1987 NHL Draft. Fleury played in the NHL for four teams, Calgary Flames from 1988 to 1999, Colorado Avalanche during the 1998-99 NHL season, New York Rangers from 1999 to 2002, and Chicago Blackhawks during the 2002-03 NHL season. He won the Stanley Cup with the Flames in the 1988–89 NHL season. Fleury also won a gold medal with Team Canada in the 2002 Winter Olympics.