The previous longest match was at the French Open in 2004, when Fabrice Santoro beat Arnaud Clement after six hours and 35 minutes.
Arguably his major claim to fame is playing in the longest match of all time at Wimbledon in 2010, though he has beaten Federer and Djokovic.
Federer had to dig deep to beat the former U.S. Open champion 3-6 7-6 19-17 in four hours 26 minutes, the longest match in Olympic tennis history.
Two years after winning the longest match in grand slam history, No.10 John Isner was at it again as he faced France's Paul Henri-Mathieu in a marathon encounter.
Isner, who was involved in the longest match in tennis history at Wimbledon in 2010, won the game and then broke the Argentine's serve in the next to set up a clash with Spanish 18th seed Feliciano Lopez.
The Frenchman overcame American John Isner in the second-longest match in French Open history in the previous round, which lasted five hours 41 minutes, but he could not repeat the effort as he went down in another five-setter 6-4 6-4 1-6 4-6 6-1.
It was the longest tennis match in history measured by games and elapsed time.
On court for three hours and 29 minutes it is the longest recorded match in the season-endning tournament's history.
Nadal quickly dismissed fears his comprehensive defeat was because of an injury sustained in his marathon match against Moya on Saturday, the longest three-set match on the ATP Tour in 15 years.
Speaking of sports, you have probably already forgotten the names Nicolas Mahut and John Isner , but their feat of carrying on the longest pro tennis match in history will likely last forever.
The Australian Open record for the longest men's match was set in 2009, a five-setter between Rafael Nadal and Fernando Verdasco that Nadal won in 5 hours, 14 minutes.
Wilson Chandler had 16 points, and Corey Brewer and Kosta Koufos added 13 points apiece for the Nuggets, who need one win to match their longest home winning streak, from Jan. 28-April 20, 1989, despite missing Lawson.
Rubin, though, stuck boldly to her task and dragged it back to 4-4 - only for her 30-year-old rival to break her again in by far the longest game of the match and then comfortably hold serve to clinch victory.
The match was the longest Wimbledon men's singles final ever at four hours, 48 minutes, and the winning shot was struck with Centre Court in near darkness at 2115 BST.
Another empty-handed season and this will match Arsenal's longest barren spell since the 1960s.
Frindall, the longest serving member of the Test Match Special team, took particular delight that his birth coincided with the first day of the "timeless Test" between South Africa and England in Durban on 3 March 1939, a game which lasted an unprecedented 11 days.
The longest at Wimbledon was the 1989 second round match between Greg Holmes and Terry Witsken in 1989, which took five hours 28 minutes, although arguably the most famous endurance battle was between Pancho Gonzales and Charlie Pasarell in 1969, which took five hours 12 minutes and finished 22-24 1-6 16-14 6-3 11-9 to Gonzales.
In no time, though, Simon had won the next two sets and put one of Federer's longest-standing records in jeopardy: Before the match, he had reached at least the quarterfinals at 35 consecutive major events.
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