Novak Djokovic on Thursday got knocked out early at the Monte Carlo Masters for the third year in a row, prolonging the top-ranked Serb's quest for a record-extending 39th Masters trophy.
Playing in only his second match on clay this season after a one-month pause, Djokovic lost 4-6, 7-5, 6-4 against Lorenzo Musetti in the third round of the Monte Carlo Masters Thursday.
Still adapting to the slow surface, Djokovic struggled with his movement, hit 46 unforced errors and could not find a solution to counter his Italian rival's solid baseline shots.
A two-time champion at Monte Carlo, Djokovic lost his opening match on the French Cote d'Azur last year and exited the tournament in the third round in 2021.
Djokovic got off to a strong start but lost control of the match in the second set, dropping his serve five times as both players struggled with accuracy in windy conditions.
Djokovic led 4-2 but could not hold onto his lead as Musetti’s mix of clever drop shots and deep groundstrokes put the 22-time Grand Slam winner on the back foot. Djokovic was broken at love in the 11th game and was furious at the changeover, stomping on his racket and destroying it.
Musetti kept his cool in the next game to serve out the set and force a decider.
The match was suspended by rain for about an hour with the score 6-4, 5-7, 1-1 and Djokovic up 40-30 on his serve. Musetti broke for a 4-3 lead and concluded on his fourth match point.
The 16th-seeded Musetti, who led two sets to love against Djokovic at the 2021 French Open before retiring in the fifth set, will take on Jannik Sinner in the quarterfinals.
The seventh-seeded Sinner came from behind and saved a match point to get past No. 10-seeded Hubert Hurkacz 3-6, 7-6 (6), 6-1.
Sinner trailed by a set and a break before coming out on top of a 22-shot rally when down 6-5 in the tiebreaker to remain in the match. Hurkacz lost the following two points and threw his racket in anger, before totally losing his focus in the decider.
"Playing against him, I knew already from the beginning that it was very tough to get into the rhythm,” Sinner said. "I think he served incredible in the first one-and-a-half sets, and when I broke him the first time the momentum changed a little bit.”
Also, German qualifier Jan-Lennard Struff took another step in his comeback from an injury as he upset fourth-seeded Casper Ruud 6-1, 7-6 (6).
Having been ranked 29th, Struff dropped as low as No. 168 after sustaining a foot fracture last year during a match in Miami, an injury that left him sidelined for more than two months.
Struff has enjoyed a good start to the season and returned to the Top 100 last month but had not beaten anyone in the Top 10 since June 2021. His aggressive style of play resulted in 37 winners and 23 points won at the net against Ruud, who dropped his serve four times.
Struff ended Ruud's nine-match winning streak on clay. The 2022 French Open runner-up had won his past two tournaments on the surface, in Gstaad last July and in Estoril last week.
Struff will next be up against 2021 runner-up Andrey Rublev, who beat Karen Khachanov 7-6 (4), 6-2 at the Country Club.
"We know each other too well," Rublev said. "The first set was only mental. We didn’t show some tennis skills. But it was tough to show skills because the wind was really hard and the court was slippery and it was tough to do something.”
Two-time defending champion Stefanos Tsitsipas defeated Nicolas Jarry 6-3, 6-4 without dropping his serve.
"I had to deal with a few (tough) points, especially when he had break points,” said Tsitsipas, who next plays eighth-seeded Taylor Fritz. "I dealt with those situations very maturely and played precisely, so it was great out there.”
Sixth-seeded Holger Rune advanced to the quarterfinals without playing when Matteo Berrettini withdrew due to an injury. Third-seeded Daniil Medvedev was scheduled to play 13th-seeded Alexander Zverev later.