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Martina Navratilova
Martina Navratilova defected from Czechoslovakia to the United States in 1975 at 18, seeking the freedom to pursue tennis professionally without the constraints of the Czechoslovak sports federation, and went on to build one of the most decorated careers, across singles and doubles combined, the sport has ever produced. She won 18 Grand Slam singles titles, including a women's-record nine Wimbledon singles championships, and added 31 more major titles in women's and mixed doubles, for 59 Grand Slam titles overall across singles and doubles combined — a total unmatched by any player of either gender in the modern era. Navratilova's rivalry with Chris Evert, playing out across 80 professional matches from 1973 to 1988, is one of the longest and most closely contested rivalries in tennis history, with Navratilova finishing 43-37 in the head-to-head, and the two players' contrasting styles — Navratilova's aggressive serve-and-volley game against Evert's disciplined baseline consistency — pushed women's tennis forward through the entire late 1970s and 1980s. She held the world No. 1 ranking for 332 total weeks across singles and doubles, and continued competing at a high level well into her 40s, winning her final Grand Slam title, mixed doubles at the 2006 US Open, at age 49 — a level of longevity that remains without real precedent in professional tennis.
VS
Novak Djokovic
Novak Djokovic turned pro in 2003 and, by the time he'd finished his run through the sport's record books, held more Grand Slam singles titles than any player in tennis history, male or female — 24 majors, passing both Rafael Nadal's and Roger Federer's totals despite starting his career slightly behind both of them. Djokovic holds the record for most weeks spent at world No. 1, more than 400 total, and won a record 10 Australian Open titles, making Melbourne Park the site of his single greatest tournament dominance the way clay was for Nadal and grass was for Federer. He completed the career Grand Slam, winning all four majors at least once, and in 2021 came within one match of the first calendar-year Grand Slam in men's tennis since 1969, losing the US Open final after winning the season's first three majors — a near-miss that still stands as one of the closest any player has come to the feat in the modern era. Djokovic's game is built on a foundation of elite return of serve and defensive flexibility that made him exceptionally difficult to hit through, a style that took longer to earn the same popular affection as Federer's or Nadal's but that ultimately produced the most statistically decorated career of the three.
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