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#2 Roger Federer
The man widely considered to be 'The Greatest of All-Time' is just two short of winning an even 100 Singles' titles. The only man to have won the 'BBC Overseas Sports Personality of the Year' a record four times has continued to play tennis at the highest level well into his late thirties unlike greats from earlier eras. This has greatly contributed to Roger Federer's popularity across generations of tennis fans and have also helped him rake in substantial amounts of prize money over the years. The winner of a record 20 Grand Slam titles and 6 ATP Tour Finals has amassed a career-prize money of $117,773,812 till date.
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