Wilkinson, who played football in Southampton as a youth and auditioned unsuccessfully at Aston Villa and Coventry City , turned pro tennis in 1989 at the age of 18. He mostly played on the ATP Challenger Tour , where he was able to win three singles and five doubles titles over the course of his career. He was less successful on the ATP World Tour . His biggest individual success was the quarter-finals at the Queen's Club Championships after victories over Jared Palmer and Goran Ivanišević . In doubles, he was twice in an ATP final, 1997 at the Bournemouth Open and the Nottingham Open . He reached his highest ranking in the tennis world rankings in 1993 with position 114 in singles and in 1998 with position 86 in doubles.
His best individual result at a Grand Slam tournament was reaching the third round at Wimbledon , which he achieved four times and defeated players like Marc Rosset , Carlos Costa and Jonas Björkman . In the doubles competition he reached the quarterfinals of Wimbledon at the side of his compatriot Paul Hand von 1993 , including a victory against Luke and Murphy Jensen , who had recently won the double title at the French Open .
Wilkinson played five individual games for the British Davis Cup team between 1991 and 1998 . His record was 2: 3. His greatest success with the team was the first round participation in the world group in 1998, which was won 3-2 against India . Wilkinson lost his single game against Mahesh Bhupathi .
At the 1992 Summer Olympics , he competed in singles and doubles for Great Britain. In singles he failed in his first round game to Younes El Aynaoui , in doubles he was eliminated in the first round at Andrew Castle's side against the doubles pairing from Argentina .
After finishing his professional career, Wilkinson worked as a commentator and columnist for ESPN .