Andy Murray’s Wimbledon run came to an end when he lost to Canadian tenth seed Denis Shapovalov, proving to be a step too far on his singles comeback.
Murray, a two-time champion, was defeated by left-hander Shapovalov 6-4, 6-2, 6-2.
Murray’s defeat came after American prodigy Sebastian Korda ended British number one Dan Evans’ bid to reach the last 16 for the first time.
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Evans, 31, had not dropped a set in his first two matches, but was defeated by the SW19 debutant 6-3 3-6 6-3 6-4.
With Murray and Evans out, Cameron Norrie is the only British man who can reach the second week of this year’s tournament in singles.
On Saturday, Norrie will face eight-time champion Roger Federer, while the final Briton in the women’s singles, 18-year-old Emma Raducanu, will face Sorana Cirstea.
Shapovalov said after beating former world number one Murray, “This is a dream come true for me. I put in countless years of hard work to play on Centre Court and to play Andy in a match like this.
“He is truly an inspiration to many people – including me. It is amazing to be here and I don’t think I could have played any better.”
Murray defied the odds yet again with thrilling victories in his first two matches, but the 22-year-old Shapovalov represented a significant step up in class.
Murray got off to a sluggish start in the first two sets, trailing 5-1 in both as the Canadian demonstrated his talent, and even the Scot found this challenge insurmountable.
He beat Georgian 24th seed Nikoloz Basilashvili and German qualifier Oscar Otte in dramatic fashion, surviving a wobble in the first and fighting back to win a dramatic five-setter in the second.
Murray returned rejuvenated under the roof after the players were called off due to darkness in both of those matches.
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Another forced break before the third set could not help the Scot this time, against an energetic opponent who hit a total of 42 winners.
Shapovalov refused to back down under the spotlight. The world number 12 continued to make Murray work in his service games and dominated his own in the third set to take a 5-1 lead.
Murray, the 2013 and 2016 champion, left to another standing ovation after a mature performance that was capped off with an ace.