Andy Murray failed to convert three match points as he lost in the first round to Alex De Minaur at the China Open in Beijing.
The 24-year-old Australian battled his way to a 6-3 5-7 7-6 (8-6) victory over the former world number 1 in a fifth meeting between the pair, with De Minaur winning all five, including in the first round at Queen’s earlier this year.
He took the first set thanks to a single break in the second game of the match, but a succession of backhand errors in the second set gave Murray the chance to level the match.
The two-time Wimbledon champion showed his frustration and was given a code violation for slamming his racket on the ground after allowing his opponent to break serve, but he recovered his composure to level everything on one set .
Murray had two match points at a 5-2 lead in the deciding set, but De Minaur held serve before beating the 36-year-old in the next game. That eventually led to a tie-break, in which the Australian took a 5-2 lead.
Murray hit back with four straight points to set up his third match point, but he dropped both his serves and was defeated again at the hands of De Minaur.