Novak Djokovic's hopes of becoming the first man to win a calendar Golden Slam were crushed by a semi-final defeat to Alexander Zverev at the Tokyo Olympics.
From a set and a break up, Djokovic dropped a staggering eight games in a row on his way to a 1-6 6-3 6-1 loss.
The 34-year-old Serbian had been unsure about coming to the Games but was swayed by the pride he takes in representing his country and the tantalising opportunity to add a gold medal to a potential clean sweep of the grand slams.
He has already won the Australian Open, French Open and Wimbledon, and will head to the US Open in August as a heavy favourite regardless of this setback.
But this was just not Djokovic's day, despite him making a whirlwind start and dominating until the point he broke to lead 3-2 in the second set. From there, Zverev seized control.
When Djokovic volleyed into the net to make it 3-3, dropping serve for the first time in the match, it looked like just a minor stumble.
Yet suddenly he was struggling for form and did not win another game until he was already 4-0 behind in the deciding set.
Zverev was playing blindingly brilliant tennis and was proving obdurate too, saving four break points in the second game of the third set.
He clinched victory with a blazing backhand winner, and goes on to face Russian Karen Khachanov in the final.
The result means Djokovic, like Roger Federer, seems fated never to win the Olympic singles gold medal. And it leaves Steffi Graf as the only player to ever win a calendar Golden Slam, having done so in 1988 when she added the Seoul Olympics title to her haul of majors.
Russian Olympic Committee's Khachanov fended off Spain's Pablo Carreno Busta with some ease in the first semi-final, with the world number 25 sweeping to a 6-3 6-3 victory in an hour and 19 minutes.
He won 26 of 28 points on first serve to freeze out Carreno Busta, who had only one break point all match and could not take that opportunity.
"It's just a pure happiness, a pleasure to be here to live those moments, these kind of memories will stay forever," Khachanov said.
Khachanov delivered a rock solid display, with his serve and forehand at their best, barely giving his opponent a sniff of an opportunity as the Moscow-born 25-year-old established a firm grip.
"That's the way I prepared, against every opponent you play a little bit differently," Khachanov said. "The final will be another story, another match, another day. I hope it will be the same."
Carreno Busta, who will face Djokovic for the bronze medal, said: "It was not the best match I have played, but Karen was unbelievable today, playing very aggressive and serving really good."
Emma Raducanu records impressive victory over Angelique Kerber in Stuttgart
Emma Raducanu claimed an emphatic 6-2 6-1 win over former two-time champion Angelique Kerber in the last 32 of the Porsche Grand Prix in Stuttgart.
Fresh from helping Great Britain reach the finals of the Billie Jean Cup at the weekend, Raducanu continued her promising form on clay by breezing past the home favourite.
Both Raducanu and Kerber were playing as wild cards in Stuttgart, with the Briton tumbling down the rankings after time out to undergo three surgeries.
Meanwhile former world number one Kerber only recently returned from 18 months out on maternity leave.
Raducanu got off to a flying start by breaking Kerber in the opening game and despite an immediate response from the German, the 2021 US Open champion took control and claimed the first set in 41 minutes.
Kerber was broken again at the start of the second set and although she managed to haul back level, Raducanu stepped up a gear and shrugged off a brief visit from the trainer to wrap up an emphatic win.
Also in Stuttgart, reigning US Open champion Coco Gauff rallied from 4-2 down in the deciding set to overcome fellow American and world number 134 Sachia Vickery 6-3 4-6 7-5.
And Tunisia’s Ons Jabeur finally snapped a five-game losing streak to beat Ekaterina Alexandrova 2-6 6-3 7-6 (1), telling reporters: “I thought about withdrawing so many times because I couldn’t take another loss.”
In Rouen, Naomi Osaka’s return to clay was cut short by a 6-4 6-2 first round defeat to Martina Trevisan.
Like Kerber, Osaka only recently returned to the tour following maternity leave, and was competing as a wild card.
In the Oeiras Ladies Open in Portugal, Britain’s fifth-seeded Harriet Dart suffered a 6-3 6-1 defeat to home player Matilde Jorge.
Rafael Nadal’s Barcelona Open hopes ended by Alex de Minaur
Rafael Nadal’s latest comeback bid came to an end as he was well beaten 7-5 6-1 by fourth seed Alex de Minaur at the Barcelona Open.
The 37-year-old was playing just his second tournament in 15 months after suffering another hip problem at his comeback event in Brisbane in January.
And having intimated that this will be his final year before retirement, Nadal’s defeat was likely to mark his final appearance at a tournament he has won 12 times.
Having overcome Italian Flavio Cobolli in the opening round, Nadal faced a much sterner test against the in-form De Minaur and was sent scampering around the court in a tight opening set which was edged by the Australian.
De Minaur went on to step up a gear, securing a double break over the Spaniard and racing over the line behind a strong service game on which he did not drop a single point in the second set.
Jack Draper made the most of a rain delay to defeat wild card Rudolf Molleker and reach the quarter-finals of the BMW Open in Munich.
German Molleker, ranked 179th, had been the better player in the first set but a brief stoppage ahead of the second set changed the momentum of the contest.
Draper began to assert his powerful game after the resumption and lost only two more games, pulling away to claim a 4-6 6-1 6-1 victory.
In the last eight the British number two, who is ranked 46th, will take on either third seed Taylor Fritz or Spanish qualifier Alejandro Moro Canas.
Speaking in an on-court interview, Draper said: “I think Rudy played an amazing level in the first set. The conditions were very rainy and very slow. In the second and third, the sun comes out and I start feeling better. I’m really proud of the way I played.”
Rafael Nadal eases past Flavio Cobolli on return to action in Barcelona
Rafael Nadal made a triumphant return to the match court with victory over Flavio Cobolli in the first round of the Barcelona Open.
The 37-year-old was playing just his second tournament in 15 months after suffering another injury problem in his hip muscle at his comeback event in Brisbane in January.
Nadal only committed to playing at the tournament he has won 12 times on Monday but there was not much rust on display as he eased to a 6-2 6-3 victory over 21-year-old Italian Cobolli in his first match on clay since he won his 14th French Open title in 2022.
Nadal received a hero’s welcome as he strode out onto the court that bears his name and, although there were a few loose forehands in the early stages, the former world number one was too solid for Cobolli.
Cobolli understandably looked nervous and contributed to the scoreline with far too many errors, but a big factor in that was the pressure being exerted from the other end of the court.
A blip came when Nadal, who is set to retire at some point this season, played a poor game to drop serve for the first time in the third game of the second set but he had already broken Cobolli and quickly restored his advantage.
There were some vintage forehands from Nadal in the final stages and he clinched victory when Cobolli netted a final backhand, thrusting his fist into the air.
The home favourite faces a real test next, though, when he takes on in-form fourth seed Alex De Minaur.
Meanwhile, second seed Andrey Rublev destroyed his racket at the end of a 6-4 7-6 (6) defeat by Brandon Nakashima that continued his poor run of form.
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