Lorenzo Musetti earned the biggest win of his career Thursday at the Rolex Monte-Carlo Masters, where he upset World No. 1 Novak Djokovic 4-6, 7-5, 6-4 to reach his second ATP Masters 1000 quarter-final.

Competing in wet and windy conditions on Court Rainier III, the 21-year-old Italian exploited a weak serving performance from Djokovic, breaking the Serbian eight times en route to a two-hour, 54-minute win. After converting his fourth match point, an emotional Musetti looked at his team and shook his head in disbelief.

“I am struggling not to cry,” Musetti said in his on-court interview. “It is an emotional win because it was a really long match. Three-hour match and suspended by rain. It was not easy conditions because it was a little bit windy and cold. Not like we used to play in the recent days. I am really proud of myself and I can see on the screen. I am struggling not to cry because it is a dream for me.”

After dropping the opening set, Musetti rallied from 2-4 in the second set to level. He hit with aggression and depth to force Djokovic into 11 unforced errors in the set and then continued to play with intensity and flair after a 59-minute rain delay at the start of the decider to earn the second Top 5 win of his career.

“I couldn’t find the right balance on [serve]. Particularly with the toss. I think we were returning better than serving,” Musetti said. “The rallies at the end were really intense and really long and it was a tough battle. Even for the physical and mental part. Beating Novak is something remarkable for me.”

With his ninth tour-level win of the season, Musetti improved to 1-3 in his ATP Head2Head series against Djokovic. He will next play countryman Jannik Sinner after the 21-year-old defeated Hubert Hurkacz earlier Thursday.

Djokovic began the week with an ATP Tour-leading 58.7 winning percentage behind his second serve according to Infosys ATP Stats. Against Musetti he won just 39 per cent of his second-serve points (12/31). Entering the match the Serbian had lost serve just 17 times in 17 matches this year. Against Musetti he dropped serve eight times. 

Musetti entered the clash with momentum, having defeated Miomir Kecmanovic 7-6(1), 6-0 and Luca Nardi 6-0, 6-0. The 21-year-old Italian, who is into his second Masters 1000 quarter-final after reaching the last eight in Paris in 2022, opened his shoulders as the match went on, crushing the ball off both wings to triumph.

“I am just going to enjoy this win for at least half an hour and then I will rest, recover and be ready for the next battle with a friend and fellow Italian,” Musetti added.

The 21-year-old is up to No. 20 in the Pepperstone ATP Live Rankings and would climb to No. 17 if he defeats Sinner. That would mark a new career-high for the Italian.

Djokovic was chasing a record-extending 39th ATP Masters 1000 title this week. The Serbian is a two-time champion in Monte-Carlo, having triumphed in 2013 and 2015.