Slam champion Stefan Edberg, and the Paris Masters 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. Gilbert's best performances at Grand Slam tournaments were in the Quarterfinals of the 1987 US Open, losing to Jimmy Connors and in the quarterfinals of the 1990 Wimbledon Championships, losing to Boris Becker. He was also runner-up at the inaugural Grand Slam Cup in 1990. Gilbert was ranked among the top-ten players in the U.S. for nine of his first ten years on the professional tour. His career win–loss record in singles play was 519–288. 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, at the Masters Grand Prix in 1985, which sent McEnroe into his first six-month break from tennis. Style of play Unlike many other professional players of his era, Gilbert did not have a major offensive weapon such as an overpowering serve or forehand. His best asset was his ability to keep the ball in play. He hit the ball most often at a slow but accurate pace and was sometimes called a pusher. In his 2002 autobiography, John McEnroe called Gilbert a pusher and claimed that Gilbert had the ability to bring talented players down to his type of game. In addition, McEnroe stated that Gilbert was the most negative person he had ever played tennis against, and he was riled by Gilbert's alleged non-stop tirades against himself while playing. Gilbert kept an open stance and did not turn much during the swing at the baseline. This enabled him to control the game through oversight and tempo, despite his defensive style. He built his game around destroying his opponent's rhythm. He forced his opponent into long rallies by hitting the ball high over the net and deep into his opponent's court. If an opponent employed a slow pace,