Success stories

Jackson was born in Kingston, Jamaica but grew up in Mississauga, Ontario. At the age of 15, he moved to England, where his talent was immediately identified by the ASPIRE coaching staff. He joined Rushden & Diamonds in 2004 following trials with Manchester United and Manchester City, and was the club's top scorer in the 2006-07 season, scoring 20 goals.

On January 4, 2009, Jackson scored an equalising goal for Gillingham in their 2–1 FA Cup Third Round defeat by Aston Villa. His impressive performance resulted in him being linked to a 1m move to Villa.

Jackson has seven caps for the Canadian Men's Youth (U-20) team. His first game was a friendly against Brazil in May 2006. His most recent action was at the 2007 FIFA U-20 World Cup when he played in all three of Canada's games. On November 14, 2008, he received his first call up for the Canadian senior squad for a match against his country of birth, Jamaica. He received his Canadian passport in June 2007.

Notably Simeon will go down in Gillingham history as the man who scored the goal which took the club into League One, following his last minute headed goal in the Play Off Final against Shrewsbury Town which secured promotion for the Gills.