Andy Murray suffered defeat at the round-of-16 stage in the Rotterdam Open on Thursday, losing 6-3 6-4 to Canadian Felix Auger-Aliassime, who will now face Britain's Cameron Norrie.
Murray beat the dangerous Alexander Bublik in his opening match, but he has had difficulty stringing a run of wins together since his hip operation three years ago and found the 21-year-old world No 9 too powerful.
The three-time Grand Slam winner did not manage to force a single break point in their only previous meeting, a straight-sets defeat at the 2020 US Open.
He righted that wrong by breaking in the fifth game of the first set, but Auger-Aliassime had already won the previous four games.
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The Scot, who won this tournament in 2009, clawed a break back early in the second set but smashed his racket in frustration as he immediately dropped serve again to trail 3-2.
There was a bizarre moment on match point when Murray's cap flew off, causing him to stop playing as Auger-Aliassime hit a winner.
He was afforded a let, but Auger-Aliassime duly went on to convert a second match point for a 6-3 6-4 win and a meeting with Norrie in Friday's quarter-finals.
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