Fleming attended
Chatham High School, where he won the New Jersey high school individual championship in 1972, during his junior year. He won the men's singles in the
Ojai Tennis Tournament in 1975. During the 1980s, Fleming teamed up with fellow American
John McEnroe to dominate the men's doubles game. The duo won 52 doubles titles together, including four at
Wimbledon (1979, 1981, 1983 and 1984), and three at the
US Open (1979, 1981 and 1983). Fleming once said that "The best doubles pair in the world is John McEnroe and anyone". Fleming also played on three American
Davis Cup winning teams (
1979,
1981 and
1982), and helped the US win the
World Team Cup twice (1984 and 1985). Fleming reached the World No. 1 doubles ranking in 1984. His career-high singles ranking was world No. 8 in 1980, the year in which he reached the quarter-finals at the Wimbledon championships. Over the course of his career Fleming won three top-level singles titles and sixty doubles titles. Prior to turning professional, Fleming played tennis for the
University of California, Los Angeles (after transferring from the
University of Michigan), and won the
National Collegiate Athletic Association doubles title in 1976. Since retiring as a player, Fleming has become a tennis commentator for
Sky Sports,
Eurosport and the
BBC. Fleming is a keen golfer (handicap 10) and is an active member of The Stage Golf Society. He was inducted into the
Intercollegiate Tennis Association (ITA) Hall of Fame. On July 30, 2011, Fleming, the
Farmers Classic 1979 singles and 1983 doubles champion, was named
2011 Farmers Classic Tournament Honoree. In 2020 five of Fleming's Wimbledon Lawn Tennis Championships Medals, dating from 1978 to 2002, were found in London and reported to the
Portable Antiquities Scheme. ==WCT, Grand Prix, and Grand Slam finals==