Jackson was born in Kingston, Jamaica but grew up in Mississauga, Ontario. He played for his local team in Canada, Sunoco FC. He was invited to have trials with Gillingham, but was rejected by the club. At the age of 15, he moved to England and lived with his grandmother in Croydon.
Rushden & Diamonds
He joined Rushden & Diamonds in 2004 and was the club's top scorer in the 2006–07 season, scoring 20 goals. The next season he was top scorer for the Diamonds in the league, scoring 16 goals, despite leaving for Gillingham in January. He was joint 8th top scorer in the league that season. In 2005, he had trials with Manchester United and Manchester City. Jackson went on a one-month loan to Raunds Town in December 2005. When he left the Diamonds he had established himself as the club's eighth highest......
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