World number one Novak Djokovic suffered a first defeat to Casper Ruud as he was beaten in the semi-finals of the Monte-Carlo Masters.
Norwegian Ruud delivered the biggest win of his career with a 6-4 1-6 6-4 victory to reach his second ATP Masters 1000 final.
Ruud had never won a set off Djokovic in their past five meetings, but found his form against the tournament’s top seed to battle through to the final, where he will face Stefanos Tsitsipas.
In a rematch of last year’s French Open final between the pair, Djokovic – who had appeared to struggle physically during his quarter-final win over Alex De Minaur – failed to find his usual high levels.
Ruud, though, rose to the occasion on Court Rainier III to hold off a fightback from the Serbian in the final set, with Djokovic recovering from 4-1 down to level.
The 25-year-old rallied to claim a third match point after Djokovic double faulted, completing a hard-fought victory in two hours and 17 minutes.
Djokovic, meanwhile, sees his hunt for a first tournament win of 2024 continue.
“I am super happy. This is a day I will remember for a long time,” Ruud told the ATP Tour website.
“Beating a world number one is something I have never done and beating Novak is something I have never done.
“I am very, very happy. I am a little bit in a state of shock right now.”
Earlier, Tsitsipas had battled past second seed Jannik Sinner 6-4 3-6 6-4 and now has his eyes set on a third title in the Principality.
“It was tennis at its highest level that I have been able to play,” said the Greek, who lifted back-to-back Monte-Carlo Masters titles in 2021 and 2022.
“Jannik was an extremely-difficult opponent and it can be seen throughout the year so far.
“He has been very consistent and I could see that throughout today with his game.
“He is one of the toughest opponents I have faced so far and to find ways when there weren’t that many, I am proud of that.”
Nadal slumps out of Madrid Open as farewell appearance comes to a halt
Jiri Lehecka claimed a memorable win over one of tennis' greats as he downed Rafael Nadal at the Madrid Open.
Nadal's farewell appearance at the tournament he has won five times came to an end with a 7-5 6-4 defeat on Tuesday.
The 22-time grand slam champion had been hoping to tee up a quarter-final against Daniil Medvedev.
Ultimately, though, world number 31 Lehecka was the man who progressed.
Lehecka ruined the hopes of the Nadal fans packed into the stands in the Spanish capital, and took control when he reeled off 10 straight points to take the opening set.
Nadal won the Madrid Open in 2008, 2010, 2013, 2014 and 2017, and said farewell to the crowd in an on-court interview following his defeat.
Data Debrief: Nadal falls short of milestone
Nadal had been hoping to win his 60th match at the Madrid Open, while he would have reached his 100th ATP Masters 1000 quarter-final had he won. This was his first defeat to a player ranked lower than 20th in the world since he went down to Pablo Cuevas in 2016.
Lehecka, meanwhile, will make his second appearance in the last eight of a Masters 1000 event.
Auger-Aliassime gets the better of Ruud as Medvedev hits Masters 1000 milestone
Casper Ruud's hopes of building on his victory at the Barcelona Open were ended as he lost to Felix Auger-Aliassime at the Madrid Open.
Auger-Aliassime will now face top seed Jannik Sinner in the quarter-finals, after claiming a 6-4 7-5 victory over the fifth seed Ruud on Tuesday.
Ruud, runner-up at last year's French Open and a force to be reckoned with on clay, won in Barcelona earlier in April, but came unstuck against the Canadian.
It was not the only shock exit, as Alexander Zverev, the world number five, succumbed in straight sets to Francisco Cerundolo.
Earlier, Daniil Medvedev claimed his place in the quarters, in which he could face Rafael Nadal, by beating Alexander Bublik 7-6 (7-3) 6-4.
Data Debrief: Medvedev's milestone
Five of the six quarter-finals Medvedev has reached on clay have come at either ATP Masters 1000 or grand slam level.
He has now reached at least the quarter-final stage at all nine Masters events, too.
Alcaraz matches Nadal record as reigning champion scrapes into Madrid Open quarters
Jan-Lennard Struff made life difficult for Carlos Alcaraz, but the reigning Madrid Champion eventually made it through.
Alcaraz had won both of his opening games with the minimum of fuss, but he needed three sets to get beyond Struff, who won a second-set tie-break.
However, Alcaraz eventually prevailed in the decider, clinching a 6-3 6-7 (5-7) 7-6 (7-4) victory.
Alcaraz, who is in the hunt for a third straight title in Madrid, will now face seventh-seed Andrey Rublev for a place in the last four.
Data Debrief: Prodigal son matches the master
There have been plenty of comparisons between Alcaraz and his fellow Spaniard Rafael Nadal.
And with his win on Tuesday, Alcaraz matched Nadal's record for the longest winning run at the Madrid Open, at 14 matches, since the tournament began in 2002.
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