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.”
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Jannik Sinner has withdrawn from the Madrid Open due to a hip injury ahead of his scheduled quarter-final clash with Felix Auger Aliassime.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.
Alcaraz sees Madrid Open reign ended by Rublev in last eight
Carlos Alcaraz saw his hopes of a third straight Madrid Open crown dashed on Wednesday, as Andrey Rublev fought back to seal a statement quarter-final win over the defending champion.
Alcaraz had been pushed close in the last 16 by Jan-Lennard Struff on Tuesday, requiring two tie-breaks to see off the German in three sets, and those exertions seemed to take their toll as he produced a below-par display on Wednesday.
Seven unforced errors from Rublev helped the home favourite take the opener, but he appeared to tire from there as his seventh-seeded opponent fired in 27 winners in a 4-6 6-3 6-2 victory.
Rublev broke Alcaraz's serve in the first and fifth games of the decider, also serving impressively to deny the Spaniard a single break point after a nervous first hold.
Alcaraz's exit ended home interest in the tournament, just one day after five-time champion Rafael Nadal was dumped out in the last 16 by Jiri Lehecka.
Speaking to Sky Sports Tennis, Rublev said: "I can't believe that I was able to stay calm throughout the match. I didn't say a word and even I'm impressed by that!
"I want to believe that I have been working on this because if not, then I'm stupid. I just thought to myself to keep trying, keep fighting, keep believing in yourself."
Data Debrief: Major scalp for Rublev
To say Rublev entered Wednesday's match as the underdog would be an understatement. Alcaraz was looking to become the first player to win three straight Madrid Open singles titles, and was 24-0 in Spanish clay-court events since the start of 2022.
Rublev, though, was not overawed by the occasion and punished a sluggish performance from the world number three. Wednesday's win was his first over a top-three opponent since 2022, and he will now face either Taylor Fritz or Francisco Cerundolo in the last four.
Rybakina saves two match points to beat Putintseva in Madrid Open quarter-finals
Elena Rybakina saved two match points as she outlasted Yulia Putintseva to win a dramatic encounter 4-6 7-6 (7-4) 7-5 in the Madrid Open quarter-finals on Wednesday.
The world number four was on the brink of defeat at 5-2 down in the third set, with her fellow Kazakhstani Putintseva eyeing a third win in as many head-to-head meetings between the pair.
However, Rybakina came up with one of the shots of the tournament on Putintseva's first match point, capitalising on a drop shot clipping the net cord to produce a nonchalant winner.
The 2022 Wimbledon champion didn't look back from that moment on, producing back-to-back breaks before holding her nerve through a tense final service game, converting her fourth match point to wrap up a gruelling two-hour, 48-minute contest.
Rybakina has now won 16 successive matches on clay, and she will face either Aryna Sabalenka or Mirra Andreeva in the semi-finals on Thursday.
Data Debrief: Rybakina rampant
Rybakina is the form player on the WTA circuit, with Wednesday's win her 30th of 2024, more than any other player.
She is just the second player to win 30 or more matches in tournaments starting within the first four months of a calendar year, after Iga Swiatek managed 32 victories during the same span in 2022. Swiatek, of course, went on to win the French Open and US Open titles that season.
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