During his second season as a pro he made his NHL debut when he was called up to Toronto and appeared in five games. The following year he doubled his totals playing ten games with the Leafs and 37 more with Newmarket. In 1989-90 he logged 21 games with the Maple Leafs sharing duties with Allan Bester and Mark Laforest. The following season he upped his totals to 30 games backing up rookie Peter Ing who won the starting job in Toronto. A year later, the Maple Leafs made a blockbuster trade to bring inHall of FamerGrant Fuhr to handle the goaltending duties allowing Reese to apprentice in the crease behind Fuhr but it was a short lived arrangement because Reese himself was soon part of an enormous trade. On January 2, 1992, Reese was included in a ten-player trade that also sent Craig Berube, Alexander Godynyuk, Gary Leeman and Michel Petit to the Calgary Flames in exchange for Doug Gilmour, Jamie Macoun, Kent Manderville, Ric Nattress and Rick Wamsley.
Calgary Flames
With the Flames, Reese became the backup to incumbent Mike Vernon and parts of three seasons in Calgary and played 26 games in 1992-93 posting an impressive 14-4-1 record. The highlight of his time in Calgary came on February 10, 1993, when he entered the NHL record book by posting three assists in a 13-1 Flames victory. With the emergence of first round draft pickTrevor Kidd in the Flames net, Reese was out of a job and found himself on the move early in the 1993-94 season when Calgary traded him to the Hartford Whalers in exchange for defenseman Dan Keczmer.
Hartford Whalers
In Hartford, he was acquired to back up Sean Burke. When Burke struggled with back issues, Reese and goaltender Frank Pietrangelo each logged 19-games in the Hartford crease. Much like in Calgary before, the emergence of a younger netminder - this time Jason Muzzatti - pushed him out and led to a trade to the Tampa Bay Lightning.
Tampa Bay Lightning
Tampa Bay had a solid starting goalie in Daren Puppa but his backup, Jean-Claude Bergeron was struggling for the Lightning so the veteran Reese took over the duties and acquitted himself well with a 7-7-1 record in 19 appearances. During the off-season, he was on the move again when he was sent to New Jersey in a swap for goaltender Corey Schwab.
New Jersey Devils
With the Devils, Reese was slotted behind Martin Brodeur but quickly lost his backup job to rookie Mike Dunham and instead spent the majority of the 1996-97 season with the Detroit Vipers of the International Hockey League, splitting time with starting goaltender Rich Parent. The duo combined to win the James Norris Memorial Trophy, allowing the fewest goals in the league. The Vipers went on to win the 1997 Turner Cup. Reese was the starting goaltender for the Vipers during the 1997-98 season. He was named to the All-IHL Second Team in both 1997 and 1998.
Return to the Toronto Maple Leafs
As an unrestricted free agentin the summer of 1998, Reese's career went full-circle when he signed with the Toronto Maple Leafs organization. The Maple Leafs signed goaltender Curtis Joseph that summer as well and had planned to deal incumbent Felix Potvin away, but when that trade didn't transpire, that started the season with both Joseph and Potvin on the roster pushing Reese down to the minors. He would play his final two NHL games with the Maple Leafs while also playing 27 games with the St. John's Maple Leafs of the American Hockey League. He was traded back to Tampa Bay in the off-season so they would have a veteran goalie to expose in the 1999 NHL Expansion Draft. He was not selected by the Atlanta Thrashers and retired that summer.
Coaching career
After retiring Reese worked as a goalie coach with the Lightning organization and won a Stanley Cup with them in 2004. On June 25, 2009, he was hired by the Philadelphia Flyers as their goalie coach, replacing Réjean Lemelin. On March 6, 2015, Reese and the Flyers management mutually agreed to part ways. On June 15, 2015 he joined the Dallas Stars as their goaltending coach.