Grigor Dimitrov came out strong but faded fast as the Winston-Salem Open's top seed was forced to retire from his match against Dominic Thiem, sending the Austrian into the round of 16.
With less than a week to go before the start of the US Open, Dimitrov came out sharp, unleashing a torrent of backhanded slices to keep Thiem off balance as the Bulgarian raced through the surprisingly one-sided first set 6-0.
But things took a turn for the worse for Dimitrov at 2-2 in the second and he began to misfire in bunches in an apparent attempt to shorten points.
After a visit from medical staff, he stepped up to the line to serve while trailing 2-4 but decided he was feeling too unwell to continue and shook hands at the net, where he waited for Thiem while hunched over.
The win gives another lifeline to 2020 US Open champion Thiem, who had to save two match points to win his rain-delayed opener against American J.J. Wolf the day before.
Thiem will next face either Italy's Fabio Fognini or Britain's Jack Draper.
Earlier in the day, France's Benjamin Bonzi, Australia's Jason Kubler and Americans Maxime Cressy and Steve Johnson were among those who advanced in straight sets at the ATP 250 tournament in North Carolina.
An 83rd-minute Weverton own goal from a deflected Malo Gusto cross gave Chelsea a nervy 2-1 win over a spirited Palmeiras side in the Club World Cup quarter-finals on Friday.
Women's top seed Aryna Sabalenka fought off inspired home favourite Emma Raducanu in a cauldron-like Centre Court atmosphere to keep her Wimbledon quest on track but it was the end of the road for two other Grand Slam champions on Friday.
India finished day three of the second test on 64-1 to lead England by 244 runs after they dismissed the hosts for 407 in the first innings at Edgbaston on Friday despite Jamie Smith's commanding and unbeaten knock of 184.
There were to be no Fourth of July celebrations for American Madison Keys as she joined the exodus of seeds from Wimbledon with a 6-3 6-3 defeat by 104th-ranked German Laura Siegemund in the third round on Friday.
Prime Minister Luis Montenegro joined members of Diogo Jota’s family for a private wake on Friday in the Liverpool footballer’s hometown in northern Portugal following his death alongside his brother Andre Silva in a car crash in Spain.