A Port Kembla local and Dapto junior, Simon made his first grade debut with the Steelers aged 17 and went on to make 120 appearances for the club between 1990 and 1995. He received the BHP Medal as the Illawarra Steelers' player of the year in 1994. In 1996 Simon moved to the Sydney City Roosters but was unable to dislodge Adrian Lam from the first grade half spot and he moved to Parramatta for three seasons from 1997 to 1999. In the 1998 preliminary final against Canterbury, Parramatta were ahead 18-2 with less than 10 minutes to play. After Canterbury scored a try to make it 18-6, Simon had two chances of a field goal that would have given Parramatta the victory but missed both attempts. After missing the second attempt, Simon was substituted off the field by a frustrated Brian Smith. Canterbury went on to win the game 32-20 in extra time. His apparent lack of fitness found him out of favour with coach Brian Smith and midway through 1999 he gained another release to play for Auckland. After two seasons with the Warriors, Simon moved to the Wests Tigers where, despite some good performances for the club, he announced his retirement before the end of the 2001 season citing a lack of enthusiasm. The Tigers had been beaten 64-0 by Melbourne that weekend. In 2003 Simon was named in the commemorative Illawarra "Team of Steel" celebrating players from 25 years of the club's history.
Representative career
He was selected at half-back for City Firsts in 1991 and 1992 and in game I of the 1992 State of Origin was picked in the run-on side when Ricky Stuart was unavailable due to injury. The Blues won the match but Stuart regained his spot for game II. It would be another five years before Simon would again wear the Blues' jumper. During the 1997 season, split at both club and representative level due to the Super League war, Simon appeared in all three games, once at half and twice off the interchange bench. Simon was the Blues' hero in game II, landing a 26-metre field goal in the 67th minute that clinched New South Wales' 1 point win. In 1997, Simon made his sole national representative appearance, selected for Australia in the one-off Test against a Rest-of-the-World side at Suncorp Stadium.
Post-career
After retiring, Simon worked in Aboriginal Education, before buying a Subway in Kiama in 1997. He coached at a local level, including the Illawarra Titans in a Kooriknockout competition.
