Shields grew up in North Bay, Ontario, playing minor hockey until bantam level with the local Athletics AA program of the NOHA. At age 16, Shields moved to southern Ontario to play for the St. Marys Lincolns Jr.B. club of the OHA before accepting a scholarship to the University of Michigan. As a collegiate player, Shields became the first goalie in NCAA history to record 100 career victories and was a two-time All American. Shields was drafted in the fifth round in the 1990 NHL Entry Draft by the Buffalo Sabres out of the University of Michigan. Shields was a journeyman NHL goaltender over his tenure. In his NHL career, Shields would play for the Buffalo Sabres, San Jose Sharks, Mighty Ducks of Anaheim, Boston Bruins, Florida Panthers, and Atlanta Thrashers.
One of his career highlights was during the 1997 playoffs, when Dominik Hašek was injured. Hašek had been the team MVP and the league's best goalie during the regular season and he had been considered crucial to the Sabres' playoff hopes. With Hašek leaving in the midst of game three of the first round, Shields was forced to step in but he helped the Sabres to rally and defeat the Ottawa Senators. Shields then played the second round series against the Philadelphia Flyers, as Hašek was suspended for three games after an altercation with reporter Jim Kelley. Hašek was set to return in game four with the team down by three games in the series, but he told the Sabres' coaching staff he felt a twinge in his knee and left the ice after the pregame skate. Shields turned in another season-saving performance as Buffalo staved off the almost inevitable sweeping elimination with a win. Again before the fifth game, Hašek declared himself unfit to play and Shields would finish the series with Buffalo losing 6–3 and being eliminated.
Shields's best season was in the 1999–2000 season, when he played in 67 games for the San Jose Sharks while posting respectable goaltending numbers for the team. San Jose made it to the second round of the playoffs that year.
Goalie mask design
Shields had a notable goalie mask which was designed while he was a member of the Boston Bruins during the 2002-03 season. Shields's mask was a tribute to former Bruins goalie Gerry Cheevers famed "stitch mask". He continued wearing the stitch mask after he was traded to the Florida Panthers, and being signed by the Atlanta Thrashers.
Coaching career
Shields served under Mel Pearson as a volunteer assistant coach at Michigan Tech for two seasons from 2011 to 2013 before joining the Florida Panthers as a goaltending consultant in the summer of 2013. On May 7, 2015, it was announced that Shields was named a volunteer assistant coach for the Michigan Wolverines men's ice hockey team.