Matheson played collegiate tennis in the United States, first at the University of Oklahoma and then Arizona State University. He appeared in the main singles draw at Wimbledon twice and was beaten in the first round on each occasion, to Joao Cunha-Silva in 1993 and David Wheaton in 1995, both in four sets. He is the club manager at AELTC (2015)
Matheson is the son of Harry Matheson, who competed in the 1963 Wimbledon Championships.
His mother Carole was also a tennis player.