Top seed Stefanos Tsitsipas lost in straight sets in the Queen’s quarter-finals to Canadian teenager Felix Auger-Aliassime.
Tsitsipas, 20, lost 7-5 6-2 to the 18-year-old eighth seed.
Auger-Aliassime took the first set by breaking his Greek opponent’s serve when leading 6-5.
The teenager saved three break points to take a 4-1 lead and hit a backhand out of Tsitsipas’ reach to break serve and win the match.
“He’s the most difficult opponent I’ve ever faced, and I think it’s going to take a couple of tries to beat him,” said Tsitsipas, who has faced Auger-Aliassime.
“It’s upsetting, obviously, that he’s better than me. I have to accept that.”