A trademark Andy Murray fightback was in vain as the former world number one was defeated by Czech teenager Jakub Mensik in the second round of the Qatar Open.
Facing an opponent half his age, Murray - who had made his ATP Tour debut months before Mensik was even born - broke while the 18-year-old twice was serving for the match but eventually succumbed to a 6-7[6] 7-6[3] 6-7[4] loss in a gripping three-hour and 23-minute battle.
Mensik's triumph also saw the 2005-born protege reach an ATP Tour quarter-final for the first time in his embryonic career, and he will face top seed Andrey Rublev or French wildcard Richard Gasquet in his last-eight battle.
"I'm just speechless right now, I don't know what to say," Mensik said on the court. "Tough, tough match today, Andy is a brilliant player, I know that, I watched him win Wimbledon twice on TV. It's amazing that he can still compete with the best players in the world and good luck to him for the next tournament.
"First set it was tough with the conditions, the tie-break was not so good quality, but I was a little bit lucky in the end. I tried to stay calm, I'm so happy I stayed focussed until the end."
While Murray had written his own headlines in his opening contest with Alexandre Muller, which saw him end a six-match losing streak for his first win of 2024, Mensik entered the second-round affair on the back of a shock two-set win over fifth seed Alejandro Davidovich Fokina.
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The Czech youngster came out firing on Wednesday, reeling off a succession of aces and winners in the early exchanges and breaking for a 2-1 lead, but while serving for the set, Mensik was unable to hold his nerve as Murray earned a timely break back.
However, the 36-year-old squandered two set points as Mensik produced his own mini-comeback in the tie-breaker, and neither man would lose serve in the second set, but Murray had two break points which he failed to put away.
Nevertheless, the Briton was firmly in his groove and opened the second set tie-breaker with four successive points to take the contest to the distance, much to the elation of the Doha crowd.
There was some concern for Murray at the start of the third set, as the Briton took a tumble on the court and was in visible discomfort, but he was helped up by Mensik and managed to soldier on.
Mensik's sympathies did not extend further than hauling Murray to his feet, as he broke the Briton straight off the bat and had one foot firmly in the last eight when he repeated the trick in the seventh for a 5-2 lead.
In typical Murray fashion, though, the three-time major winner did not crumble in the face of adversity and incredibly reeled off a four-game winning streak to fashion the third tie-breaker of the match.
The Briton's powers of recovery quickly waned, though, as he sent a backhand wide to bring up two match points for Mensik, whose final forehand into the corner could only be returned into the net by Murray.
