#2 Roger Federer - Wimbledon
Roger Federer has won 20 Grand Slam titles in his career, the highest by any male player ever. He won his first Gram Slam in 2003, where he defeated Mark Philippoussis 7-6, 6-2, 7-6, and that marked the beginning of his dominance.
Federer has won 6 Australian Open titles, 1 French Open title, 8 Wimbledon titles and 5 US Open titles. His tally of 8 Wimbledon titles is the highest by an individual in the Open era.
Federer has reached a record 30 Grand Slam finals, which includes a streak of 10 consecutive finals from 2005 Wimbledon to the 2007 US Open.
The 37-year-old is just one title away from completing a century of titles; he has won 99 so far, which is the second highest in the Open Era after Jimmy Connors who won 109 titles.
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