Novak Djokovic’s quest for a record-extending 39th Masters trophy was prolonged on Thursday after the world number one fell to a 4-6 7-5 6-4 defeat at the hands of Lorenzo Musetti.

Djokovic’s defeat to the Italian came in the third round of the Monte Carlo Masters.

The Serbian’s last meeting with Musetti on clay was a gruelling Roland Garros clash in 2021.

In that game, he battled back from two sets down to win, but this time it was the Italian that claimed a comeback victory in windy conditions.

Both players struggled on 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.

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

Musetti will next face fellow Italian Jannik Sinner, who beat Hubert Hurkacz.

Seventh seed Sinner was made to toil by Hurkacz in a 3-6 7-6(6) 6-1 win.

Watched on by sprint great Usain Bolt, Hurkacz took a 3-0 lead in the opening set before wrapping it up with two fiery first serves.

After the pair traded breaks at 2-2 in the second set, Sinner saved a matchpoint in the tiebreak and dragged the contest into a decider.

The Italian then got his nose in front and held firm to complete the win as Hurkacz faded.

Defending champion Stefanos Tsitsipas eased past Nicolas Jarry in just over 90 minutes, saving two break points to claim a 6-3 6-4 victory and extend his winning streak at the tournament to 12 matches.

Russian Andrey Rublev beat compatriot Karen Khachanov 7-6(4) 6-2, while American Taylor Fritz dispatched Jiri Lehecka in three sets.

German qualifier Jan-Lennard Struff stunned fourth seed Casper Ruud 6-1 7-6(6), ending the Estoril champion’s nine-match winning streak on clay stretching back to last July.

In-form third seed Daniil Medvedev, the winner of four hardcourt tournaments in 2023, will take on Alexander Zverev in the pair’s first clay court meeting.

Italian Matteo Berrettini earlier withdrew from his meeting with sixth seed Holger Rune due to an abdominal injury, sending the Danish teenager through to the last eight.

(Reuters/NAN)