Career
Simpson began his professional career with Tivoli Gardens F.C., and scored the winning goal in a final round victory over Arnett Gardens F.C. to lead the club to the 2009 Jamaican National Premier League title. Simpson made a few appearances for the Jamaica national football team in friendlies that were part of the build-up to the 2009 CONCACAF Gold Cup. Simpson was attacked and stabbed to death in Kingston, Jamaica, on 13 October 2009.
Before the kick-off of each Jamaica league game on Sunday 18 October, a minute of silence was observed in his memory.