Wilkison became a professional tennis player in 1977 and was in the singles finals of Auckland , in which he lost to Vijay Amritraj . The following year he won his first individual title on the ATP World Tour in Sydney by beating Kim Warwick in the final . In 1980 he celebrated his first double title in Manchester at the side of John Sadri . In total, he won six singles and ten doubles titles in his career. He achieved his highest world rankings in 1986 with position 23 in singles and 1989 with position 21 in doubles.
He achieved his best result in a Grand Slam tournament in 1986 at Wimbledon when he was the last American to be eliminated in the quarter-finals against Stefan Edberg . In the doubles competition he was in the semifinals of the Australian Open and Wimbledon in 1979 . In the same year he was also in the quarter-finals of the US Open .
After his professional career he played on the ATP Seniors Tour. In 1998 he won his first victory over Jimmy Connors at the Nuveen Masters Championships , to whom he had been defeated in eleven games since 1979. It had its best ranking in the world ranking of senior citizens with position 15 in 2000.
He got his nicknames Doctor Dirt and Rambo because of his aggressive style of play and his pike jumps. Vitas Gerulaitis said of Wilkison “ Every match I've played with him he always comes out bleeding. One of these days, he's going to kill himself ”(German:“ After each of our games he was bleeding. At some point he'll kill himself ”)