Simpson attended Donald Quarrie High School and Hydel High School in Jamaica and played club soccer for Sporting Central Academy before joining the youth academy of Canadian team Vancouver Whitecaps joining Jamaica youth national teammate Dever Orgill.
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.
After featuring for Sporting Central Academy most of his career, Simpson move to Portmore United in January 2011.
He spent 18 months with North East Stars FC of the TT Pro League from September 2012.
On 30 May 2014, he made his debut for the Jamaica senior team against Switzerland, as a second-half substitute in Lucerne.