Novak Djokovic’s quest for a record-extending 39th Masters trophy was prolonged on Thursday after the world No.1 fell to a 4-6, 7-5, 6-4 defeat at the hands of Lorenzo Musetti in the third round of the Monte Carlo Masters.

Djokovic’s last meeting with Musetti on clay was a gruelling Roland Garros clash in 2021, in which he battled back from two sets down to win, but this time it was the Italian that claimed a comeback victory in windy conditions.

Still adapting to the slow surface, Djokovic struggled with his movement in a sloppy display, dropped his serve eight times and could not find a solution to counter his rival’s solid baseline shots.

“Well, am feeling terrible after playing like this, honestly,” said Djokovic, who is expected to resume his preparations for the French Open next week at the Srpska Open in Bosnia-Herzegovina.

Both players struggled with their serve in a contest littered with 15 breaks of serve, but Djokovic appeared to have the match in hand as he comfortably took the first set.

However, Musetti refused to go down without a fight and the Italian stepped on the gas in the second set to level the topsy-turvy encounter.

Not even a lengthy halt in play due to rain could dampen Musetti’s momentum, and the 21-year-old once again took advantage of a weak serving performance from Djokovic to break and take the win.

“I’m struggling not to cry. It was a really long match, not easy conditions. It was a bit windy, cold,” Musetti said.

“I’m really proud of myself. The rallies were long, it was a tough, physical battle. Beating Novak is something remarkable for me.”

Musetti will next face fellow Italian Jannik Sinner.

Sinner, watched by sprint great Usain Bolt, came back from a set down to beat Hubert Hurkacz 3-6, 7-6 (8-6), 6-1.

Tsitsipas bows out

Russian Andrey Rublev overcame some second-set nerves to dispatch German qualifier Jan-Lennard Struff and reach the semi-finals with a 6-1, 7-6 (7-5) victory on Friday.

Rublev will next face Taylor Fritz, who upset two-time defending champion Stefanos Tsitsipas 6-2, 6-4 to reach the semi-finals.

Second seed Tsitsipas was on a 12-match winning streak on the French Cote d’Azur, where he claimed his two Masters 1000 titles.

“I stuck to the strategy of pulling the trigger and not letting him dictate with his forehand,” the No. 8 seed Fritz said. Fritz raced to a 4-0 lead in the opening set, which he wrapped by winning his service game to love. Tsitsipas broke back to 4-4 in the second set, but then Fritz broke his serve easily for 5-4 and closed out the match with an ace for a love hold.

Tsitsipas improved slightly in the second set, only for Fritz to break decisively for 4-3 with a winner. He then held firm to set up a semi-final meeting with Rublev.

Rublev lost the first game on his serve before bagging six in a row in a quick opening set, but Struff, the world number 100, found his stride in the second as the fifth seed showed signs of nerves.

Rublev broke for 4-3, only for Struff to break back in the following game and force a tie-break, in which the Russian regained his composure to prevail on his second match point.

The top two seeds have now been knocked out of the clay-court tournament following Novak Djokovic’s exit in the third round on Thursday.