Andy Murray suffered defeat in the second round of the Rotterdam Open as he fell in straight sets to Felix Auger-Aliassime, while Andrey Rublev and Stefanos Tsitsipas progressed.
Murray, who triumphed at this tournament in 2009, battled past Alexander Bublik in his opening match but struggled to replicate that form against Auger-Aliassime on Thursday.
The Scot was never in control against the world number nine, who will face Murray’s fellow Briton Cameron Norrie in the quarter-final, as he was downed 6-3 6-4 by the third seed.
“From the start of the match I was ready and focused and I think that is why I was able to produce a high level from the first point,” Auger-Aliassime said on court after his victory.
“He made me bring out my best tennis and I am really happy with the way I played and that I was able to stay ahead. [To] win in straight sets is a great relief.”
Top seed Tsitsipas, who was a beaten semi-finalist in this event last year, made light work of Ilya Ivashka as he raced to a 6-4 6-1 triumph in just one hour and 11 minutes to tee up a last-eight meeting with Alex de Minaur.
Reigning champion Rublev cruised past Soonwoo Kwon in similar fashion with a 6-3 6-3 win to secure his seventh straight victory at the ATP 500 tournament.
Meanwhile, qualifier Jiri Lehecka recovered from a first-set scare against Botic van de Zandschulp to succeed 1-6 6-4 6-4, with Lorenzo Musetti awaiting the Czech in the next round.