On 13th July 2004, Norwich manager Nigel Worthington surprised the Norwich fans and the media when he announced that Bolton defender Simon Charlton had flown out to Kuala Lumpar to sign for the Canaries who were in Malaysia on a pre-season tour. Simon signed a two year contract which cost Norwich £250,000

Simon's playing career began with his hometown side of Huddersfield for whom he made 124 league appearances between 1989 and 1993. He moved to Southampton where he made114 appearances before joining Birmingham where he spent three seasons. He then joined Sam Allardyce's Bolton where he also spent three seasons

Simon made his competitive debut for Norwich on August 14th 2004 in the 1-1 Premiership draw with Crystal Palace

In March 2006, it was confirmed that Norwich would not be renewing Simon's contract in the summer of 2006 when it expires.

Simon returned to the North West on 8th August 2006 when he joined Oldham. He retired the following summer after making 25 appearances for Oldham, scoring once

Simon returned to Norwich in the summer of 2007 where he is the Under 13s & Under 14s skills coach. He is studying for his UEFA "B" License

In April 2009, he was appointed as manager of Ridgeons League side Mildenhall Town replacing Richard Skelly. Chairman Martin Tuck said: "Simon's appointment is fantastic news for the club. The knowledge that he has gained during his professional playing career, being managed by the likes of Sam Allardyce, Alan Ball and Graeme Souness, is certainly invaluable. Simon's many football related qualifications, along with his extensive experience in coaching top young players at Oldham Athletic and Norwich City, made him the ideal appointment."

Charlton said "You look around and it's difficult to get your first break in the professional game unless your best mate is the manager somewhere. “I started right at the bottom as a player and worked my way up and I was watching a documentary about Brian Clough the other day and he said something similar when he first started out as a manager. I felt I was coming to the end of my time at Norwich's academy and wanted to have a go at senior football. This opportunity came about so I decided to give it a shot. I met the chairman, chief executive and secretary last week and they are ambitious as well as. They want to take the club forward and I believe I can help.”

In May 2010, Mildenhall won the Cambridgeshire Invitation Cup, beating Wisbech 3-1 in the final.

The following month, Charlton quit as Mildenhall's manager due to "unforseen circumstances and opportunities."

As of September 2011, he works as a Football Coach for the Global Soccer Network, an organisation which looks after the interests of several UK-based African players and many new talents within the game

In May 2012, he appeared for the Sealand national football team in a match against the Chagos Islands. The match was held at the grounds of Godalming Town

He currently is a summariser of Bolton Wanderers games for BBC Radio Manchester.