 He featured in matches against the youth academies of Eintracht Frankfurt and Leicester City at the XXIX Dallas Cup, and played in the USL Premier Development League with the Vancouver Whitecaps Residency team in 2009.He also traveled to Germany with the club and competed against the U-19 team of Hertha Berlin and others.After featuring for Sporting Central Academy most of his career, Simpson move to Portmore United in January 2011.