Andy Murray missed a match point and suffered a final-set capitulation as he bowed out to Australia's Alex de Minaur in the first round of the Paris Masters.
At 5-2 up in the decider with a double break, the three-time Grand Slam winner was ostensibly on his way to a first-ever victory over De Minaur, who had won the opening five ATP Tour meetings between the pair.
However, Murray ran out of steam towards the end and let his frustration get the better of him, as a revitalised De Minaur won five games on the spin to prevail 7-6[5] 4-6 7-5 in just over three hours.
Clashes between De Minaur and Murray have been commonplace in 2023, as the duo locked horns at the Monte Carlo Masters, Queen's Club and last month's China Open, with the Australian winning all three, although he had to beat away several Murray match points in Beijing.
Errors reared their ugly heads for Murray right off the bat, as a double fault in his opening service game gifted De Minaur the first break of the match, and the Australian was imperious on serve during the early exchanges.
However, Murray broke back to love in the eighth game and had three chances to close out the set in the 10th, but De Minaur saved all three break points before holding his nerve in the tie-breaker.
A first-game break for Murray in the second set was met with a swift response from De Minaur, but the Australian displayed a propensity for mistakes on the forehand side and lost his serve again in the ninth game, allowing the world number 40 to level the match.
As was the case in the second set, Murray broke the 24-year-old immediately in the decider and was on the cusp of ending his hoodoo against De Minaur as he repeated the trick in the seventh game, but the Australian was not giving up the ghost.
Murray squandered his first chance to serve out the contest before bringing up his first match point in the 10th game, but a shanked forehand saw a place in the second round slip from his grasp, and two netted cross-court attempts remarkably saw De Minaur break back for a second time.
The Briton went to smash his racquet on the court before thinking better of it, but he showed no mercy to the equipment several minutes later, as De Minaur came from 15-40 down to force a deuce in the 12th game.
Murray thought he had clipped the line with a forehand, only to be denied by a brilliant overrule by the chair umpire - replays showed that his shot was a fraction too long - and on De Minaur's first match point, Murray struck the net tape and excruciatingly watched the ball bounce back over to his side.
Now six for six against the two-time Wimbledon champion at the top level, De Minaur will meet France's Benjamin Bonzi or Serbia's Dusan Lajovic in round two, while Murray has now been knocked out at the first hurdle in Paris three years running.
