It was a rough afternoon for the American men at the U.S. Open.

With tears in his eyes, No. 6 Ben Shelton removed himself from Friday’s third-round match against France’s Adrian Mannarino with a shoulder injury, bringing a sudden end to the 22-year-old’s run at Flushing Meadows.

About an hour later, No. 17 Frances Tiafoe suffered an upset loss to Germany’s Jan-Lennard Struff in straight sets.

Shelton retired from the action after dropping the fourth set against Mannarino at Louis Armstrong Stadium. The match would have gone to a decisive fifth set had Shelton been able to continue.

“When he started to have pain, he was leading in the match,” Mannarino, the world’s 77th-ranked men’s player, said in his post-match on-court interview. “Honestly, he would have probably won that match.”

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