Roger Federer’s quest for a sixth US Open title came to a shocking end on Tuesday, as the No. 3 seed was defeated in five sets by Grigor Dimitrov in their quarterfinal match.

US Open Roger Federer
Roger Federer struggled with upper back and neck pain before losing in five sets to Grigor Dimitrov in the US Open quarterfinals on Tuesday. (Image: Tim Clayton/Corbis/Getty)

Dimitrov hung tough with Federer throughout the match, then ran away with the final set to claim a 3-6, 6-4, 3-6, 6-4, 6-2 victory.

Back Issues Limit Federer

Federer came into the match as an overwhelming favorite, having beaten Dimitrov in all seven of their previous meetings. But the two fought on equal terms Tuesday night, until problems with his upper back gave the 20-time Grand Slam winner trouble late in the match, allowing Dimitrov to shut the door.

Federer – who has never retired from a match in his professional career – even took a medical timeout following the fourth set. But it didn’t seem to help, as Dimitrov was able to jump out to a 4-0 lead in the final frame.

“Just disappointed it’s over, because I did feel like I was actually playing really well after a couple of rocky starts,” Federer said after the match. “It’s just a missed opportunity, to some extent.”

Dimitrov also noticed that his illustrious opponent wasn’t himself on this night.

“He started slowing down a little bit,” Dimitrov told reporters. “For sure, in the end, he was not 100 percent of himself.”

Dimitrov now moves on to his third career Grand Slam semifinal, and his first since the 2017 Australian Open. There, he’ll face Daniil Medvedev, who beat Stan Wawrinka 7-6 (8-6), 6-3, 3-6, 6-1 earlier on Tuesday. Medvedev has opened as a -178 favorite in the semifinal over Dimitrov (+150) at FanDuel Sportsbook.

Serena Almost Perfect vs. Wang

While one legend fell on Tuesday, another demolished her opponent. Serena Williams powered her way into the US Open semifinals by defeating No. 18 Qiang Wang 6-1, 6-0 in a 44-minute match on Tuesday night.

Williams rolled to a quick 5-0 lead in just 15 minutes, then dropped her only game of the match before shutting out Wang in the second set. Williams won 50-15 in total points, and Wang finished the match without a single winner.

“It feels good,” Williams said of her current form. “It feels like, ‘OK, this is what I’ve been training for. This is how hard I’ve been working.’ It feel like, you know, hard work pays off when that happens.”

Serena will next play No. 5 Elina Svitolina, who defeated 16th-seeded Johanna Konta 6-4, 6-4 on Tuesday. While Williams has a winning record against Svitolina overall, the Ukrainian did beat her at the 2016 Summer Olympics, and has been playing well throughout the US Open. Williams has opened as a -280 favorite in their semifinal match.

The remaining US Open semifinalists will be determined on Wednesday. On the women’s side, Belinda Bencic (-174) takes on Donna Vekic (+148), while Canadian teenage sensation Bianca Andreescu (-196) battles Elise Mertens (+166). In men’s play, Matteo Berrettini (+174) will take on Gael Monfils (-205), while No. 2 seed Rafael Nadal (-2000) looks to get past Diego Schwartzman (+1280).

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