He graduated from Newark Academy in 1995 and became a professional tennis player the following year. He won his first double title in 1997 in Newport and in the same year the Hopman Cup alongside Chanda Rubin . At the side of Venus Williams , he won the mixed at the Australian Open and French Open in 1998 . With 63rd place, he achieved his highest single placement on April 9, 1999. In 2006 he lost the ATP final in Newport against Mark Philippoussis .
In June 2008, Gimelstob made negative headlines when, in the run-up to a mixed show match against Anna Kurnikowa , he insulted her as a "slut" who he wanted to "hammer a serve right in the stomach", and players like Nicole Vaidišová , Tatiana Golovin and Alizé Cornet chauvinistically called "sex bombs" that would be too stupid for school and had "no social skills". Gimelstob, who was fined by the WTA , later apologized for his derailments.
^ Tennis official Justin Gimelstob serves up sexist rant against top female players , www.telegraph.co.uk, June 27, 2008; Relevant passages: "In a radio interview, the 31-year-old American lashed out at Anna Kurnikowa, calling her a bitch ... Rounding off his barrage of insults, he added, 'Female tennis players lack the social skills - they don 't go to high school, they don't go to parties.' ... He labeled France's Tatiana Golovin, ranked 21 in the world, a 'sexpot', described the Czech Nicole Vaidisova, seeded 18th at Wimbledon, as' a well developed young lady 'and called France's Alize Cornet, number 17,' a little sexpot '... He was venomous in his attack on the Russian Miss Kournikova:' She's a bitch ... I just despise her to the maximum level just below hate. ' He said he wanted to hit her hard in the midriff when serving at her. "