Fleming attended Chatham High School, where he won the New Jersey high school individual championship in 1972, during his junior year.
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 (including the 1979 Cincinnati Open) 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.
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.
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