Andy Murray's Wimbledon preparations suffered a harsh setback as he lost in straight sets to Alex de Minaur in the first round of the Queen's Club Championships on Tuesday.
The three-time Grand Slam winner was seeking an 11th successive grass-court win to continue his positive build-up to SW19, but he lost 3-6 1-6 to the Australian in one hour and 25 minutes.
On the back of successive Challenger triumphs in the Surbiton Trophy and Nottingham Open, Murray sought to prolong his purple patch at the ATP 500 event in the hope of sealing a seeding for Wimbledon.
However, the home favourite was overwhelmed by De Minaur's athleticism and accuracy on the day, winning just 29% of points behind his second serve and hitting 10 winners compared to the Australian's 20.
De Minaur saved three break points in his opening service game before breaking Murray for a 3-2 lead, and an unforced error from Murray on set point in game nine also proved costly.
The Briton kept his mistakes to a minimum throughout the affair, but an inspired De Minaur won five of the first six games of the second set to put one foot firmly in the second round.
In typical Murray fashion, the 36-year-old dug deep to save three match points, but there was to be no miraculous fightback from the Briton, as De Minaur set up a clash with Diego Schwartzman in the second round.
Murray's early exit was one of two defeats for the British men at Queen's, as Liam Broady failed to build on a fast start against Adrian Mannarino in a 6-1 4-6 3-6 defeat to the world's number 46.
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Despite the 97-place gap separating them in the rankings, Broady - down at 143rd in the world - won the opening five games thanks to a succession of errors from Mannarino, who ceded the first set with a whimper.
Broady soon went a set and a break up, but Mannarino refused to give up the ghost and fought back admirably to level the match before bringing out the winners in the final set, sealing his win with a love hold.
Over at the Birmingham Classic, Murray's fellow Nottingham champion Katie Boulter also had her celebrations cut short in a 5-7 5-7 defeat to China's Zhu Lin in the first round.
Boulter earned the first break of the contest to love in game three before consolidating with a hold to 15 for a 3-1 lead, but a trio of double faults helped Lin, who broke back for 3-3 before taking her second set point.
A frenzied second set saw three breaks apiece in the first eight games, but Boulter crucially squandered another four chances to break her Chinese counterpart, who missed two match points in the 10th game before making no mistake in the 12th.
Boulter's defeat meant that Jodie Burrage - whom she beat in the Nottingham showpiece event - could have overtaken her as British number one by reaching the final, but her run also came to an early end at the hands of compatriot Harriet Dart.
Despite taking the opening set, Burrage went down 6-4 2-6 5-7 to fellow wildcard Dart in two hours and 18 minutes, inconsequentially saving 11 of the 15 break points she faced.
Dart's reward is a second-round tie against Ukraine's Anhelina Kalinina, whom she saw off in straight sets during last week's Nottingham Open.
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