Dustin Brown's Olympic experience came to a painful end.
Brown led Brazilian Thomaz Bellucci, 6-4, 4-5, when he rolled his left ankle, attacking net for a volley and crashed to the court.
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The tearful German tried to play through the injury, but could not continue and retired sending Bellucci into the Rio second round.
"I'm happy to be in the second round but I am very sad to see a friend with a serious injury," Bellucci said afterward. "I hope it will not be too serious and hope to see Dustin soon on the tour. I am happy to be in the second round. It was very tough conditions today, it was very windy and for both players it was not easy to play so I'm just happy to be in the second round."
Brown visited a doctor for treatment where he got some bad news.
Photo credit: ITF Olympic Tennis