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Andy Murray has battled to a major career milestone in Dubai, defeating Denis Shapovalov in the first round of the ATP 500 event on Monday, 4-6, 7-6 (5), 6-3, for his 500th career hard-court win.

The three-time Grand Slam champion and former world No. 1 is just the fifth man in the Open Era to reach that number, joining four of the biggest legends in the sport on a very exclusive list.

MOST CAREER HARD-COURT WINS (men, Open Era):
783: Roger Federer [783-155]
700: Novak Djokovic [700-126]
592: Andre Agassi [592-158]
518: Rafael Nadal [518-150]
500: Andy Murray [500-174]

Murray was informed of the stat in his on-court interview.

“Yeah, it’s not bad,” he joked.

“Obviously hard courts have been a great surface for me over the years, and yeah, 500 is a lot of matches, so I’m very proud of that.

“The list that you’ve given there, there’s not many players that have done that, so yeah, great to get to 500 before I’m done.”

Murray was just two points from defeat against Shapovalov in the second set tie-break on Monday.

Murray was just two points from defeat against Shapovalov in the second set tie-break on Monday.

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After dropping the first set to Shapovalov, Murray was in even more trouble in the second set, having to fight off two break points serving at 1-all, another break point serving at 4-all—which would have given the Canadian a chance to serve for the match—and even coming within two points of defeat at 5-all in the tie-break.

But he snuck out that marathon 75-minute second set and then broke straight away in the first game of the third set, hanging onto that break until he had a 5-3 lead before grabbing one last break to close out the match after two hours and 31 minutes on court.

Murray won seven more points in the grueling encounter, 103 to 96.

“It wasn’t easy, but I managed to get it done in the end,” he added.

Up next for Murray in the second round will be one of two Frenchmen—Ugo Humbert, the No. 5 seed this week, or Gael Monfils, a wild card into the draw. They’ll play on Tuesday.