Andy Murray slipped to a straight-sets defeat against Canadian young gun Felix Auger Aliassime at the Rotterdam Open.
Murray beat the dangerous Alexander Bublik in his opening match, but he has found it difficult to string a run of wins together since his hip operation three years ago and found the 21-year-old world number nine 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.
The Scot, who won this tournament in 2009, clawed a break back early in the second 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 Great Britain’s Cameron Norrie in Friday’s quarter-final.