MONTE CARLO - Novak Djokovic was knocked out in the last 16 of the Monte Carlo Masters by Lorenzo Musetti in three sets on Thursday after the world number one struggled badly on serve.
Djokovic, a two-time winner in the Principality in 2013 and 2015, was broken eight times before going down 4-6, 7-5, 6-4 to the 21st-ranked Musetti on a wet and chilly day on the Cote d'Azur.
"(The) feeling is terrible after playing like this, honestly. But congrats to him. He stayed tough in important moments, and that's it," said Djokovic.
The Serb led by a set and a break against Musetti, but the Italian youngster fought back in a scrappy second set and then prevailed in the decider after rain interrupted the match for an hour.
Musetti advances to a quarter-final meeting with compatriot Jannik Sinner, who saved a match point before beating Poland's Hubert Hurkacz 3-6, 7-6 (8/6), 6-1.
Djokovic, the big favourite in the absence of Rafael Nadal and Carlos Alcaraz, surged 5-2 ahead in the opening set. He dropped serve as he tried to close it out before breaking Musetti for a third time.
The top seed again looked in control at 4-2 in the second but was broken easily in a game that started with Djokovic justifiably unhappy over a line call that went against him.
Musetti won the next three games, successfully serving for the second set at the second attempt after blowing his chance while leading 5-4.
A rain shower early in the deciding set forced play to be suspended, with Musetti landing the decisive break to go 5-3 up and eventually sealing victory on his fourth match point.
"I am struggling not to cry because it is a dream for me," said Musetti, who led Djokovic by two sets at Roland Garros in 2021 before having to retire.
"Beating Novak is something remarkable for me."
Djokovic, holder of a record 38 Masters titles, has not gone beyond the last eight in Monte Carlo since 2015.
"I don't think it's catastrophic, but my feeling is bad right now because I lost the match. That's all," said Djokovic.
"It's not a great day for me, so I'm not really in the mood to speak."
French Open finalist Casper Ruud also bowed out after suffering a 6-1, 7-6 (8/6) defeat to German Jan-Lennard Struff, who has beaten the Norwegian on all three occasions they have met.
The 100th-ranked Struff -- who came through the qualifiers -- will play Andrey Rublev in the quarter-finals after the Russian beat his compatriot Karen Khachanov 7-6 (7/4), 6-2.
Ruud was on a run of nine successive victories on clay -- having won in Gstaad last July and then Estoril on Sunday -- but he looked out of sorts in Monaco.
The world number four, who also reached the US Open final last year, saved two match points and fought back from 5-2 down to lead 6-5 in the second set only for Struff to level.
The German then took a hard-fought tie-break when Ruud sent a return out.
The in-form Daniil Medvedev saved two match points in a final-set tie-break to outlast Alexander Zverev 3-6, 7-5, 7-6 (9/7) under the lights.
Zverev served for the match in the second set and again in the third before Medvedev once more wriggled out of trouble in the tie-break to record his 26th win in 27 matches.
"If he'd been right mentally he could have finished the match twice," said Medvedev.
His next opponent is Denmark's ninth-ranked Holger Rune, who moved into the last eight after Matteo Berrettini withdrew due to a muscular problem the Italian suffered during his previous match.
Two-time defending champion Stefanos Tsitsipas breezed through his third-round match, the Greek swatting aside Chile's Nicolas Jarry 6-3, 6-4.
Tsitsipas goes on to face Taylor Fritz after the American eighth seed defeated Jiri Lehecka of the Czech Republic in three sets. - AFP