Simon, from West Ham. played and scored in a Devon and Exeter League against Chelston in the Autumn of 1991 whilst on trial at Exeter.

He was a youth team player at West Ham and was released by them at the end of the previous season, from Exeter he moved to Sittingbourne making his first team debut in December 1991 for them scoring both goals in a 2-0 home win over Canterbury.
He spent four years with Sittingbourne and won their 'Player of the Year' award twice before moving on in August 1995, when he signed for Hastings, becoming their club captain. He stayed with Hastings until January 1999 when he linked up with Dover.

Simon made over 100 appearances for Dover and won the club's 'Player's Player of the Year' award for the 2000/01 campaign before signing for Margate in May 2001. 

In the 2003/04 season he moved to Welling. In the summer of 2004 he retired aged 31 after undergoing two foot operations.