Jannik Sinner came of age at the ATP Finals in Turin with a first career victory over world number one Novak Djokovic.
The 22-year-old Italian won a three-hour marathon 7-5 6-7 (5) 7-6 (2) in a match of high tension and tremendous quality.
Defending champion Djokovic next faces Poland’s Hubert Hurkacz on Thursday in his final group match as he bids to reach the semi-finals.
In front of a raucous home crowd, Sinner grabbed the crucial break in the 11th game, despite finding himself 40-0 down, and then held to love to take the first set.
Djokovic, on a 19-match winning streak, took the second set to a tie-break and was twice a mini-break down before levelling the match, cupping his ear to the spectators.
World number four Sinner then played a stunning return game, breaking Djokovic to 15 with a punishing forehand to move 4-2 up in the third.
But with two hours and 40 minutes on the clock, Djokovic finally broke his young opponent for the first time in the match.
At 5-6 Djokovic began conducting the jeering crowd from his seat at the changeover.
The six-time ATP Finals champion had won 30 tie-breaks this season but number 31 proved elusive as Sinner moved 5-0 up before sealing a statement win with a smash.
“I feel I’m a bit more confident in certain moments but I still have to learn many things,” he said on Amazon Prime.
“I think I was really brave and intelligent, especially in the third set. I think we both played really well.
“It means a lot to me. When you win against the world number one who won 24 grand slams it’s up at the top.”
The afternoon match ended prematurely when Stefanos Tsitsipas retired after just 15 minutes, handing Holger Rune his first win.
Denmark’s Rune, 20, was leading 2-1 when Greek world number six Tsitsipas pulled out due to a back injury.
Tsitsipas was forced to withdraw from the tournament and was replaced by Hurkacz.
“Unfortunately, I felt terrible on the court. I did what I could do in the best possible way to be ready and fit for this match, but it didn’t work out for me,” Tsitsipas, the 2019 champion, said in his press conference.
“It kills me not to be able to finish this tournament, the one that I’ve prepped for for so long.”
Lehecka into maiden Masters semi-final after Medvedev retires hurt
Jiri Lehecka progressed to the first ATP Masters 1000 semi-final of his career as Daniil Medvedev retired hurt on Thursday at the Madrid Open.
Lehecka, who beat the great Rafael Nadal in the last 16, had just taken the first set 6-4 when Medvedev threw in the towel.
Medvedev had earlier received treatment from the physio, having seemingly struggled when moving to his right side.
"It's never easy in a match like this," Lehecka said. "If I were to choose the way how to win this match, it wouldn't be like that.
"So of course, it's never easy to see your opponent struggling, but at that moment, you just need to focus on yourself, trying to get the maximum level out of yourself."
Lehecka will face Felix Auger-Aliassime, who progressed thanks to a walkover following Jannik Sinner's withdrawal, for a place in the final.
Data Debrief: Czech mates
Lehecka is the third Czech player to reach the semi-finals in Madrid, following Jiri Vovak and Tomas Berdych.
Should Lehecka reach the final, he will move into the top 20 of the ATP rankings for the first time.
Swiatek races into Madrid Open final with dominant win over Keys
Iga Swiatek cruised into her second Madrid Open final on Thursday, maintaining her ominous form by beating Madison Keys 6-1 6-3 within 71 minutes.
Swiatek had been forced to fight back from a set down against Beatriz Haddad Maia in the quarter-finals, but there was no slow start on Thursday as she broke Keys' serve to love at the first attempt.
Only in the fifth game, when Keys failed to convert two break points, was Swiatek troubled in a 31-minute opener, and she carried that momentum into the second set with another early break.
Having eliminated Coco Gauff and Ons Jabeur on a deeply impressive run, Keys had no answer for Swiatek's power as she clinically worked her way through the second set, the American's forehand running long on match point to seal a routine win for the world number one.
Having lost last year's final against Aryna Sabalenka, Swiatek could face a rematch against the defending champion, who takes on Elena Rybakina in Thursday's other semi-final.
Data Debrief: Swiatek surpasses Serena
Saturday's final will be Swiatek's 11th at WTA 1000-level, the Pole going all the way on 37.9 per cent of her 29 main-draw entries at that level. That is a better ratio than 23-time grand slam champion Serena Williams managed in her glittering career, the American doing so at 18 of 49 WTA 1000 tournaments (36.7 per cent).
Swiatek has now played eight matches in 2024 without dropping a single game on her own serve, a tally only matched by her possible final opponent Sabalenka on the WTA tour.
Top seed Sinner withdraws from Madrid Open ahead of quarter-finals
Jannik Sinner has withdrawn from the Madrid Open due to a hip injury ahead of his scheduled quarter-final clash with Felix Auger Aliassime.
The world number two was due to face Auger Aliassime for a place in the semi-finals after fighting back to overcome Karen Khachanov in three sets on Tuesday.
However, the Italian has been advised to withdraw to avoid aggravating an issue with his right hip, which he says has troubled him throughout the tournament.
Sinner, who is 28-2 for the season and won his first grand slam title at the Australian Open earlier this year, wrote on X: "Very sad to have to withdraw from my next match here in Madrid.
"My hip has been bothering me this week and has slowly been getting more painful. Taking the advice from the doctors, we decided it's best to not play further and make it worse."
Sinner's withdrawal means Auger Aliassime will advance to his first ATP Masters 1000 semi-final since 2022, with Daniil Medvedev or Jiri Lehecka – who eliminated Rafael Nadal on Tuesday – up next for the Canadian.
On the other side of the draw, two-time defending champion Carlos Alcaraz suffered a surprise exit at the hands of Andrey Rublev on Wednesday, with the Russian set to face either Taylor Fritz or Francisco Cerundolo in the last four.
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