Kyle Edmund’s US Open run ended in tears when he retired with a neck injury in the fourth set of his third-round match against Denis Shapovalov.
The 22-year-old, Britain’s lone singles representative in the last 32, won the first set against 18-year-old Canadian prodigy Shapovalov at Arthur Ashe Stadium.
But Shapovalov fought back to level and Edmund’s chance went when the Yorkshireman appeared to hurt his neck in the fifth game of the third set.
He received three bouts of treatment but was clearly hampered and did not win another game before pulling the plug with Shapovalov leading 3-6 6-3 6-3 1-0.
It was Edmund’s 10th match in 14 days after reaching the semi-finals of the Winston-Salem Open and his heavy schedule perhaps caught up him.
Shapovalov, meanwhile, becomes the youngest man to reach the fourth round of a grand slam since Marat Safin at the French Open in 1998 and has a great opportunity to go further in a wide open section of the draw.
It was a sign of Shapovalov’s star power at such a tender age and playing in only his second grand slam tournament that this match was scheduled on Flushing Meadows’ centre court.
This was a different test for Shapovalov, who had played so freely in beating Jo-Wilfried Tsonga two days ago but now found the weight of expectation on his shoulders.
The Canadian struggled to land his signature one-handed backhand in court in the early stages and Edmund moved into a 3-0 lead.
A double fault from the British player helped Shapovalov level but the teenager was making far too many unforced errors and he was broken again to leave Edmund serving for the set.
Shapovalov had two more break points but Edmund calmly saved them both before clinching it with a fine rally.
Edmund has a serious weapon in his forehand but danger in the Shapovalov game can come from almost anywhere.
He began to turn the match around early in the second set, breaking Edmund for 3-1.
The British player saved four set points at 5-2 but could not take his one chance to get back on serve, netting a routine backhand as Shapovalov served it out, roaring in celebration.
It is only seven months since the pair first met in a now infamous Davis Cup clash, which ended in disgrace for Shapovalov when he accidentally struck umpire Arnaud Gabas in the eye with a ball hit in anger and was defaulted.
Edmund was already well on his way to winning, with Shapovalov then ranked outside the top 200 and raw.
But the talent was obvious and, although he is still ranked 27 places below Edmund at 69 in the world, the Canadian appears headed for the top 10 sooner rather than later.
He announced himself at the top level on home soil in Montreal earlier this month, beating Rafael Nadal and going on to reach his first Masters semi-final.
It is far from inconceivable to see Shapovalov going at least as far here given the complete lack of regular slam challengers in the bottom half.
Edmund was clearly very upset to see his tournament ended in such a manner, for he too would have fancied his chances of going much further.
The 22-year-old left the court in tears but can hold his head high, with the last two weeks another sign that, when Andy Murray does retire, British men’s tennis is in steady hands.
Edmund’s exit, though, made it the first time a British singles player has failed to reach the second week at a slam since the French Open in 2013, when Murray also pulled out.
Shapovalov will face Spanish 12th seed Pablo Carreno Busta in the last 16.
“It’s never good to win this way, I hope it’s not too serious,” said the world No 69.
“Kyle has been playing great tennis and if he keeps it up he will be doing really well.
“In one game he hit a second serve and I heard him grunt like he had hurt something and he called the trainer. It’s very unfortunate but I am happy to be in the fourth round.”
Jamie Murray and Bruno Soares began the defence of their US Open men’s doubles title with a straight-set win over Alexander Peya and Julian Knowle.
The British-Brazilian fourth seeds won 6-4 7-6 (8-6) in New York.