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Oldest tennis player ever. The oldest tennis player is JosÃ© Guadalupe Leal Lemus (Mexico, b. 13 December 1902) who began playing tennis in 1925 and has been playing regularly ever since, aged 101, a total of 79 years. He currently plays every Wednesday at the Club Campestre Morelia, Morelia, Mexico with a group of doctors, 20-25 years his junior.
Maureen Connolly. Maureen Catherine Connolly-Brinker (nÃ©e Connolly; September 17, 1934 â June 21, 1969) known as Little Mo, was an American tennis player, the winner of nine Grand Slam singles titles in the early 1950s. In 1953, she became the first woman to win all four Grand Slam tournaments during the same calendar year.