Novak Djokovic crashed out of the Monte Carlo Masters after a straight sets defeat to Alejandro Tabilo.
Chilean Tabilo had beaten the world number five on clay in Rome last year, and built on a solid start to the second-round match before securing a 6-3 6-4 win in just under an hour-and-a-half on Court Rainier III.
Djokovic’s wait for a 100th ATP Tour title goes on, having lost to teenager Jakub Mensik in last month’s Miami Masters final.
Tabilo, ranked 32 in the world, broke twice in the opening set, with Djokovic looking rather subdued playing his first match back on clay since winning Olympic gold last summer.
Djokovic’s wayward returns continued to prove costly as Tabilo – who beat Stan Wawrinka in the first round – built on an early break in the second before closing out an impressive victory to take his place in the last 16.
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“I just tried to remember what I did well last time (against him),” Tabilo said in his courtside interview.
“Thankfully I served well today and it helped me a lot. It was an unreal match.”
World number three Carlos Alcaraz had earlier battled to a first Monte Carlo win as he recovered after losing the opening set to beat Francisco Cerundolo 3-6 6-0 6-1.
Alcaraz had lost his previous two matches in the Indian Wells semi-finals to Jack Draper and then Miami against veteran Belgian David Goffin.
The 21-year-old, already a four-time Grand Slam champion, regrouped for the second set, before Cerundolo’s serve faltered in the decider.
“I didn’t start well. I made a lot of mistakes and I let him play inside the court, dominating the points,” Alcaraz said.
“I just knew that I had to do something else, play more aggressively, and play my own tennis: drop shots, going to the net. I tried to return closer to the line and push him.”
Alcaraz will play Daniel Altmaier in the third round after the German qualifier beat Richard Gasquet 7-5 5-7 6-2 on what was the veteran Frenchman’s last appearance in the event ahead of his intended retirement after Roland Garros.
Fourth seed Casper Ruud had little trouble as he dispatched veteran Spaniard Roberto Bautista Agut 6-2 6-1 while Alejandro Davidovich Fokina beat Argentina’s Tomas Martin Etcheverry 7-6 (2) 6-3 and will next play British number one Draper.
Seventh seed Andrey Rublev, tournament winner in 2023, marked his first match under new coach Marat Safin with a straight-sets 6-4 7-6 (2) win over Gael Monfils while Australian Alex De Minaur, France’s Arthur Fils and Italian Lorenzo Musetti were other seeds to win on Wednesday.
