Dickson, who went to school in Coburg, played his early football in the VFA with Preston. He made his Carlton debut in 1972, the same game that Alex Jesaulenko celebrated his 100th, and finished the year playing on the wing in their premiership side. Another Grand Final appearance followed in 1973 and Dickson, again playing as a wingman, finished on the losing team. In 1977 he was part of the trade which saw Peter McKenna come to Carlton but Dickson couldn't make it into the Collingwood seniors and played reserves football for the club instead.
