Ben Shelton’s US Open campaign ended in tears on Friday after he withdrew mid-match with a shoulder injury he called the “worst pain” of his life, while milestone man Novak Djokovic battled through his own physical struggles to reach the fourth round.

Canadian Open champion Shelton was locked in an entertaining contest with Frenchman Adrian Mannarino in the day’s opening match on Louis Armstrong Stadium when his tournament suddenly unravelled.

“I just did something to my shoulder, I don’t know what it is. I’m in a lot of pain,” the American sixth seed told his father and coach Bryan during a medical timeout.

As left-hander Mannarino fought back to level the match at two sets all, a devastated Shelton wiped away tears before withdrawing ahead of the decider, leaving fans gasping at Louis Armstrong Stadium.

Shelton’s compatriot 17th seed Frances Tiafoe lost 6-4 6-3 7-6(7) to big-serving German Jan-Lennard Struff at the Grandstand, while 10th seed Emma Navarro went down 4-6 6-4 6-4 to unseeded Czech Barbora Krejcikova in another upset.

As the younger generation nursed their wounds, 38-year-old Djokovic was making history under the lights of Arthur Ashe Stadium.

The Serb recovered from a lower back problem to knock out Cameron Norrie 6-4 6-7(4) 6-2 6-3, eliminating the last remaining Briton in the men’s draw and becoming the oldest man to reach the last 16 at Flushing Meadows since Jimmy Connors in 1991.

The four-time US Open winner also surpassed Roger Federer to become the man with the most hardcourt victories at the majors with his 192nd win, inching closer to a record 25th Grand Slam title.

“I’m good, man. I’m as young as ever and strong as ever,” said Djokovic after his battling victory.

Earlier in the day, 2021 champion Emma Raducanu fell 6-1 6-2 to Elena Rybakina at the same Louis Armstrong Stadium that witnessed Shelton’s anguish, as British hopes in the women’s draw ended with clinical efficiency from the Kazakh.

Defending champion Carlos Alcaraz weathered his own injury scare, overcoming knee concerns to dismantle Italian Luciano Darderi 6-2 6-4 6-0.

“It was just the game that he broke my serve, on the last point after the serve … I just felt something in the knee,” said Alcaraz, who took a precautionary medical timeout but allayed concerns with a devastating display.

“It was bothering me. But after five-six points it was gone. I was worried after that. That’s why I asked for the physio. It was nothing serious, so just for precaution.”

Defending women’s champion Aryna Sabalenka knocked out Leylah Fernandez 6-3 7-6(2) to erase the sting of her 2021 US Open semi-final upset at the hands of the Canadian.

“I really wanted this revenge,” three-times Grand Slam champion Sabalenka said.

“I’m very happy with the win.”

Elsewhere in the women’s draw, fourth seed Jessica Pegula progressed with a 6-1 7-5 victory over twice Australian Open champion Victoria Azarenka and was joined in the fourth round by former Wimbledon winner Marketa Vondrousova, who beat Italian seventh seed Jasmine Paolini 7-6(4) 6-1.

The last 16 will also feature unseeded American Taylor Townsend, who advanced with a 7-5 6-2 victory over fifth seed Mirra Andreeva in another massive upset.

Shelton, despite his heartbreak, refused to wallow in self-pity when he faced the media.

“I’ve been pretty fortunate with my life: blessings, talents, a lot of things God’s given me,” he said.

“You won’t hear me over here pouting about how bad things are with the summer that I’ve had, the things I’ve been able to do in this sport in a short amount of time and the people I got around me.”

Fourth seed Taylor Fritz lifted some of the gloom with a gritty 7-6(3) 6-7(9) 6-4 6-4 victory over Switzerland’s Jerome Kym in the last match at Ashe, becoming the only remaining American man in the last 16.

He may be joined in the next round by 14th-seed Tommy Paul, who faces Alexander Bublik on Saturday.