Simon was 11 when he joined the West Bromwich Albion youth set up, and signed professional terms with the club in July 2003. The young winger / striker went out on loan to League Tow side Kidderminster Harriers in March 2004, and again at the start of the following season, but suffered a cracked bone in his leg in October, although he was back in action five weeks later. He was recalled from his loan in December after Mansfield Town agreed at £50,000 deal for an 18 month contract. Simon went on to make 126 appearances and scoring 23 goals for the Stags although hernia operation in March 2006 prematurely ended his season. His contract was extended by a further two seasons but was released when the club were relegated to the Conference and he joined Wrexham in June 2008 on a two-year deal.

Simon arrived at Nene Park on 25 November 2008 on a loan deal until January 2009. He made his Diamonds debut in the 4-0 victory at Altrincham four days later. He returned to Wrexham at the end of his loan after making five appearances, and immediately went on loan to York City until the end of the season. After his return to Wrexham, he went out on loan again in November 2009, this time to Tamworth. On return, his contract with Wrexham was ended by mutual consent on 13 March 2010 and he joined Conference North side Eastwood Town for the remainder of the season. On 8 June 2010, he signed for fellow Conference North side Corby Town but on 13 October, he joined Southern League Premier side Hednesford Town, keeping a dual registration with Corby Town. He subsequently joined Conference North side Redditch United on 28 January 2011, but left at the end of the season, joining fellow Conference North side Worcester City on 17 June 2011.

2008/2009 - squad number 33

Conf	29.11.08	Altrincham (A)
HSCSF	2.12.08	Long Buckby (H)
Conf	6.12.08	Barrow (H)
FAT1r	16.12.08	Newport Co (A)
Conf	20.12.08	Northwich Vic(H)	as sub