Casper Ruud finally got the better of Novak Djokovic, beating the top-ranked Serb 6-4, 1-6, 6-4 on Saturday to set up a Monte Carlo Masters final against two-time champion Stefanos Tsitsipas.

Tsitsipas won the earlier semifinal against a tiring Jannik Sinner 6-4, 3-6, 6-4 to hand the Australian Open champion only his second defeat of the season.

Djokovic double-faulted on match point in his first career defeat in six matches against Ruud. The Norwegian player had never taken a set off Djokovic before, including at last year’s French Open final.

Djokovic trailed 4-1 in the deciding set but held his next serve and broke a nervous-looking Ruud’s serve to love to pull back to 4-3.

At 15-15 in the eighth game, Djokovic turned and shouted an expletive toward someone in the crowd. Chair umpire Mohamed Lahyani urged fans not to call out during a rally and did not issue a verbal warning to Djokovic despite the audible expletive, which was followed by an angry glare.

A sloppy 10th game in the deciding set saw Djokovic trailing love-40 on serve, and the eighth-seeded Ruud received the victory on his third match point.

Ruud and the 12th-seeded Tsitsipas are chasing their first titles of the year and 11th overall.

The record 24-time men’s Grand Slam champion Djokovic still hasn’t won a title this year and remains on 98 in his glittering career.

Sinner, who has three titles in 2024, looked in control in the deciding set when he led Tsitsipas 4-3 with a service game to follow. But he called for a medical timeout during the changeover, and a trainer massaged his right knee and thigh. Although a smiling Sinner shared a joke with the trainer, things got more serious in the next game when Tsitsipas broke his serve at the fifth attempt to level the score.

At the end of the next game, Sinner limped a little and clutched the hamstring area of his left leg then had both legs massaged. His movement was restricted in the ensuing game, and Tsitsipas clinched victory on his first match point when Sinner’s backhand from the back of the court went long as he struggled for balance.

“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,” Tsitsipas said.

American actress Zendaya, British actor Josh O’Connor and other cast members from the tennis movie “Challengers” were among the crowd enjoying the sunshine at Monte Carlo Country Club. Italian fans crossing the nearby border made Sinner feel at home, but Tsitsipas enjoyed strong support after winning the tournament in 2021 and 2022.

Tsitsipas broke Sinner and held for 3-1 in a commanding first set where he used angles well to disrupt Sinner’s more rhythmical play.

The level of intensity from both players increased in the second set. A long ninth game lasting 13 minutes saw the second-seeded Sinner save five break points before holding to level the match.

He broke Tsitsipas in the first game of the deciding set and held easily.

At this point, another final looked increasingly certain. Sinner was enjoying himself and smiled to his coaching team after winning one point with an audacious sliced drop shot in the fifth game.

But Tsitsipas, who took Djokovic to five sets in the French Open final in 2021, showed trademark endurance and clawed his way back as Sinner started fading.

Serbian ‘pleased’ with 70-minute victory, next faces Musetti or Fils

Novak Djokovic was delighted with his sharp play Tuesday when he kicked off his clay-court season at the Rolex Monte-Carlo Masters in dominant fashion. Despite his convincing 6-1, 6-2 victory against Roman Safiullin, the Serbian was quick to keep his expectations in check as he chases his first title of the year.

“It’s a great start. Let’s not get ahead of ourselves and put the hopes too high,” Djokovic said in his post-match press conference. “It’s only one match, but the way I felt, I’m really pleased. It’s just the beginning of the tournament. It’s one match. I’m going to hope to work tomorrow to maintain that rhythm and focus, obviously try to perform as well as I did in the second match as I did today.”

A 98-time tour-level titlist, Djokovic is 9-3 on the season, with his best result a semi-final run at the Australian Open. The Belgrade native last month suffered an early exit at the BNP Paribas Open, where he fell to Luca Nardi in the third round.

Having failed to advance beyond the quarter-finals in his seven most recent appearances in the Principality, two-time tournament champion Djokovic will hope this is the week he can return to top form and change that record. Committing just nine unforced errors and advancing after 70 minutes Tuesday was an encouraging start for the 24-time major champion.

“I really like the way I felt today on the court, the way I was striking the ball,” Djokovic said. “I think the two, three weeks of training I had is paying off. [I had a] good training block with [Nenad] Zimonjic and with the team.

“We put in a lot of hours into thinking about the game, the movement, and things that haven’t really worked for me in the first couple tournaments of this year that I played.”

The 36-year-old, who on Sunday became the oldest No. 1 in PIF ATP Rankings history, is chasing a record-extending 41st ATP Masters 1000 crown this week. Should he lift the trophy, it would mark the top seed’s third sweep of all nine Masters 1000 tournaments.

Having won in the Principality in 2013 and 2015, Djokovic will next meet Italian Lorenzo Musetti or #NextGenATP Frenchman Arthur Fils in the third round. Last year, Musetti upset Djokovic in Monte-Carlo in the same round.

“I’m not scared of anything and anybody, but I really hope that I can get the chance to play him again, get the matchup, another matchup here,” said Djokovic, who leads Musetti 3-1 in their Lexus ATP Head2Head series. “He obviously is one of the most talented players on clay, a beautiful one-handed backhand. He’s very athletic. He can do a lot of great things. He’s one of the most promising young players not only from Italy, but generally for the world.”

Asked about a potential first meeting with Fils, Djokovic also spoke highly of the 19-year-old.

“He’s only going upwards. He’s a very promising player,” Djokovic said. “He won his first title last year in Lyon. He’s a really strong guy physically. He puts a lot of weight on his shots, particularly from the forehand, and he is very athletic as well.

“Both [Musetti and Fils] are very young, promising players. Probably both of them prefer clay as the best surface for both of them. They play with a lot of spin compared to Safiullin today, [who] was playing quite flat. It’s a different matchup for me.”