Having previously been on the books at Gillingham and Dulwich Hamlet, and was signed as a scholar by Geoff Harrop. The striker has progressed through the youth ranks, and after a number of impressive performances for the reserves Simeon was named on the bench on a number of occasions.

His first taste of action in the League saw him coming off the bench in the local derby away at Northampton Town towards the start of the 2004-05 season. Simeon impressed in youth and reserve team matches, which brought him to the attention of a number of high profile clubs, and resulted in trials at Manchester United and their city rivals. Towards the end of the 2005/06 season, Simeon proved a revelation up front, scoring plenty of goals, and continuing this form into the 2006/07 season when he was the clubs top scorer with a total of 19 goals. After playing for Canada Under 20's at the Fifa Under 20's World Cup, Simeon was offered a new contract to keep him at the Diamonds until 2010.

Simeon celebrates last season