Novak Djokovic's latest bid to win a 100th career title ended Wednesday in another shock defeat to a familiar face.

Alejandro Tabilo of Chile, who handed the 24-time Grand Slam champion a surprising loss at the Italian Open last year, beat Djokovic 6-3, 6-4 in the second round of the Monte Carlo Masters in Monaco.

Back on clay, Djokovic said afterward he didn't have high expectations.

"I knew I'm going to have a tough opponent and I knew I'm going to probably play pretty bad," Djokovic, from Serbia, said. "But this bad, I didn't expect."

Djokovic, who recently lost the Miami Open final to Jakub Mensik, turns 38 next month -- shortly before the French Open starts on May 25.

Defending French Open champion Carlos Alcaraz earlier started his clay-court season by rallying to a 3-6, 6-0, 6-1 victory over Francisco Cerundolo in the second round.

The second-seeded Alcaraz was coming off a surprising loss to Belgian veteran David Goffin in his first match at the Miami Open.

Another upset seemed possible when Cerundolo, ranked No. 22, took the first set but Alcaraz dominated the rest of the match and converted five of his seven break points across the second and third sets.

Win clinched on 2nd match point

Alcaraz is seeking a second title of 2025 and to finetune his clay-court game ahead of a bid to retain his title at Roland Garros starting next month.

Tabilo clinched victory on his second match point when Djokovic returned his strong serve long.

Djokovic had saved one match point in the ninth game when he was trailing 5-3 and 30-40 on his serve, clipping a neat drop shot over the net which his Chilean opponent could not reach.

Djokovic then held for 5-4.

Other results Wednesday:

• Lorenzo Musetti, the 13th seed, beat Jiri Lehecka 1-6, 7-5, 6-2 to set up a last-16 match against fellow Italian Matteo Berrettini, who beat top-seeded Alexander Zverev on Tuesday.
• Daniil Medvedev overcame Alexandre Muller 7-6 (6), 5-7, 6-2, and fourth-seeded Casper Ruud beat Roberto Bautista Agut 6-2, 6-1.
• Richard Gasquet and Gael Monfils, a pair of 38-year-old Frenchman, were eliminated by Daniel Altmaier and seventh-seeded Andrey Rublev, respectively.

The Monte Carlo Masters is the first big clay-court tournament of the year on the ATP Tour.