After four seasons in the WHL, Reid Simpson was selected by the Philadelphia Flyers in the 1989 NHL Entry Draft. He made his NHL debut playing one game for the Flyers in the 1991-92 season. Simpson then signed with the Minnesota North Stars as a free agent in 1992, where once again he played only one game. He spent the majority of his playing time early on in the IHL and AHL.
In 1994, Simpson was traded to the New Jersey Devils and played the majority of the year with the team's AHL affiliate in Albany. Over the course of the next two seasons, Simpson spent most of his with the Devils, before having his rights dealt to the Chicago Blackhawks.
Following a short stint in the Windy City, Simpson was acquired by the Tampa Bay Lightning in the fall of 1999, before signing with the St. Louis Blues as a free agent in the summer of 2000. Simpson would miss the majority of the 2000-01 season due to injury and in the summer of 2001 joined his seventh organization, signing as a free-agent with the Montreal Canadiens. The Flin Flon, MB native played a mere 25 games with Montreal before he was claimed n waivers by the Nashville Predators.
Simpson played two season with the Predators organization before signing as a free agent with the Pittsburgh Penguins in the summer of 2003.