 Jackson was awarded the Young Player of the Month for January 2008 after scoring in three consecutive games (against Raith Rovers, Dunfermline Athletic and Stirling Albion).Jackson missed most of the 2008–09 season with an Achilles tendon injury as St Johnstone won the First Division.In July 2009 he was taken to hospital suffering from a bowel complaint that had first troubled him in April 2008, and also hindered his fitness in 2008–09.