Miles started his footballing career with Derby County getting his first team debut in the 2005/6 season.
After this he spent time on loan at Barnsley and Bournemouth before signing with the latter in July 2012.
November 2015 saw Addison signed for Peterborough United. On his debut he scored against former club Barnsley.
In March 2016, Addison joined Kilmarnock Football Club extending his contract by three years in July.