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NEW YORK—To close out a tennis match versus someone you’ve never beaten is one of the toughest tasks in sports. Doesn’t matter if it’s at the park on Sunday morning with no one watching or inside Arthur Ashe Stadium in front of the world. Then there’s doing that versus Roger Federer in the quarterfinals of the US Open.

Say hello to a day in the life of Grigor Dimitrov. In a match that lasted three hours and 12 minutes, the 28-year-old Bulgarian earned a five-set win versus Federer that was not just a breakthrough, but possibly even a career-changer. Down two sets to one, Dimitrov subsequently didn’t so much come back as charge ahead. After splitting the first four sets 3-6, 6-4, 3-6, 6-4, he dominated the fifth, going up 4-0 to coast through the decider, 6-2, and reach the semifinals here for the first time.

“I was more present,” said Dimitrov. “I was more of myself throughout every point, every game that I played. In the past, it's always been very hard to play against him.” Join the club.

Coming into this match, Dimitrov’s lifetime record versus Federer was 0-7. His pre-US Open results had hardly been encouraging, Dimitrov winning just one of his eight previous matches. Ranked 19th in the world at the start of 2019, Dimitrov this year had plummeted to No. 78. Pleasing as it is to watch Dimitrov’s versatile all-court game, the sober truth was that he often indeed personified the nickname he surely loathed: Baby Fed—a pleasant but pale imitation of the beloved Swiss genius.

Career-changer? Grigor Dimitrov earns first win over Roger Federer

Career-changer? Grigor Dimitrov earns first win over Roger Federer

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The word “genius” has been tossed around so frequently to describe Federer that it’s easy to forget that he is not a painter, scientist, sculptor, musician. Nor is he a golfer, runner or cyclist. And please be careful about comparing him to a dancer. Most of all, Federer is a competitor, engaged in a sport that hinges heavily on interaction and the ability to apply pressure to that pesky opponent. Of course, Federer is usually the big cat, delicately but genuinely strangling.

Such was how it looked early tonight, when Federer broke Dimitrov the first time he served and snapped up the opener in a tidy 29 minutes. Even when Dimitrov leveled the match – only the third time he’d ever taken a set from Federer – there was no sign of significant challenge. Why should there have been? When you never lose to someone, the one in charge issues an unspoken message: Challenge me all you want, but when push comes to shove, we both know that you will blink and remain the mouse.

With Dimitrov serving in the third at 3-3, 30-all, Federer executed a nimble chip-and-clip—a carved backhand return to Dimitrov’s backhand, followed by a backhand volley winner struck as crisply as you’ll ever see. On the next point, Dimitrov double-faulted. Blink. Two games later, Dimitrov serving at 3-5, 15-30, Federer lofted a sublime lob over Dimitrov’s head that elicited an easy overhead. Down set point, Dimitrov lined a backhand into the net. I told you. I’ll buy drinks.

Instantly, everything changed. Federer dropped his opening service game of the fourth set. Dimitrov, for so long regarded as a shot maker, was playing more like a grinder, mostly abandoning the dazzling for the quotidian. “One of the only things for me was try to keep him as much as possible on the court,” he said. “I did that very well.”

Career-changer? Grigor Dimitrov earns first win over Roger Federer

Career-changer? Grigor Dimitrov earns first win over Roger Federer

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The match leveled, Federer left the court. Federer would say later it was to treat his upper back and neck – and that most of all, he didn’t want to take away from Dimitrov’s victory. Gracious as this was, as the fifth set began, Federer was the one blinking rapidly, clearly physically debilitated. Four unforced errors handed Dimitrov a break. In the first four games, Federer won just four points.

“He mixed up well, which gave me all sorts of problems with the rhythm,” said Federer. “Could never really feel comfortable off the baseline. That's something in the past I've always been able to dominate, I'd say. That was not the case tonight. He did a good job there.”

“I think I raised my bar a little bit of my movement. I kept him in the points quite a lot,” said Dimitrov. “Just kind of make him, I felt, a little uncomfortable.”

The idea of making opponents uncomfortable—a skill Federer has mastered—might well be Dimitrov’s major breakthrough. Often in his matches, Dimitrov has wavered between bold strikes or passivity. That type of ambivalence is precisely what Federer feasts on. Not tonight, though. We shall see soon if this evening was the first day of the rest of Grigor Dimitrov’s tennis life.

Career-changer? Grigor Dimitrov earns first win over Roger Federer

Career-changer? Grigor Dimitrov earns first win over Roger Federer

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