MONACO: 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. He had never even 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, but did not issue a verbal warning to Djokovic despite the loudly audible expletive, which was followed by an angry glare.

A sloppy 10th game in the deciding set saw him 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 remained 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.

Sinner limped a little at the end of the next game 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.