Playing Career
Gilbert played tennis for Foothill College, a junior college in Los Altos Hills, California, from 1980–82, where he was coached by Tom Chivington. During this time, he won the California Junior College Singles Championship and the U.S. Amateur Hardcourt Championship. In 1981, Gilbert became a member of the American Junior Davis Cup team. In 1982, he transferred to Pepperdine University, playing for Allen Fox, where he became an All-American and reached the Finals of the 1982 NCAA Championship.
Gilbert joined the professional tour in 1982 and won his first top-level singles title later that year in Taipei. His first doubles title came in 1985 in Tel Aviv.
Gilbert won a total of 20 top-level singles titles during his career, the biggest being the Cincinnati event in 1989. He was also runner-up in a further 20 singles events, including Cincinnati in 1990 (where he lost to future International Tennis Hall of Fame inductee Stefan Edberg) and the Paris Indoors in 1987 and 1988.
Gilbert's most successful year on the tour was 1989, during which he won five singles titles, including Cincinnati, where he beat four future Hall of Famers to claim the title: Pete Sampras, Michael Chang, Boris Becker, and Stefan Edberg, as well as Agustín Moreno and Jason Stoltenberg.
Gilbert's best performances at Grand Slam tournaments were at the 1987 US Open and 1990 Wimbledon, where he reached the quarterfinals. He was also runner-up at the inaugural Grand Slam Cup in 1990.
Gilbert was ranked among the top 10 players in the U.S. for 9 of his first 10 years on the professional tour. His career win-loss record in singles play was 519–288. His career prize-money totalled US$5,509,060.
Among his upsets of players ranked in the world's top 3 were his defeat of no. 2 Boris Becker, 3–6, 6–3, 6–4, in Cincinnati in 1989, no. 2 Edberg, 7–6, 6–7, 6–4, in Los Angeles in 1991, no. 3 Sampras, 6–3, 6–4, in London in 1992, and no. 3 Jim Courier, 6–4, 6–4, at Memphis in 1994, Edberg, 6–4, 2–6, 7–6, in Cincinnati in 1989, and perhaps most significantly, no. 2 John McEnroe, 5–7, 6–4, 6–1, in the Masters in MSG New York in January 1986, which sent McEnroe into his first six-month break from tennis.
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