Midfielder Simon began his career as a youth player at Leeds United making his debut when he was just 16 years old. Two years later, having made just over 30 appearances for his home-town club, he joined Charlton Athletic for an initial fee of £500,000. He quickly moved out on loan to Ipswich though for some regular football where he scored several important goals for the club. He also spent a time with Cardiff that season, also on loan.

After just one season with Charlton, in the summer of 2007 he made the move to QPR for £200,000 but he broke his leg shortly after arriving, and upon his recovery made another loan move, this time to Hull City in January 2008 until the end of the season.