MONACO — Novak Djokovic’s ambitious pursuit of his 100th career title faced yet another setback, this time against a well-known rival.
Alejandro Tabilo, who previously surprised Djokovic with an upset at the Italian Open last year, triumphed again on Wednesday, defeating the 24-time Grand Slam champion 6-3, 6-4 in the Monte Carlo Masters’ second round.
Making his return to clay for the first time since clinching Olympic gold in Paris last August, Djokovic admitted he entered the match with tempered expectations.
“I anticipated a challenging match against a tough opponent and knew I might not perform at my best,” Djokovic reflected. “However, I never expected it to be this disappointing.”
With his birthday nearing—turning 38 next month just ahead of the French Open commencing on May 25—Djokovic is still reeling from a recent defeat in the Miami Open final against rising star Jakub Mensik.
Amidst the drama, Carlos Alcaraz, the reigning French Open champion, kicked off his clay-court season with a commendable comeback, overcoming Francisco Cerundolo 3-6, 6-0, 6-1.
Second-seeded Alcaraz, eager to shake off a surprising early exit against Belgian veteran David Goffin at the Miami Open, demonstrated his prowess by dominating the latter sets, converting five out of seven break points during the second and third sets.
As Alcaraz aims for his second title of 2025, he is focused on fine-tuning his skills on clay ahead of his title defense at Roland Garros next month.
Tabilo, who chose to represent Chile after growing up in Toronto without a deep connection to Tennis Canada, sealed his victory on his second match point when Djokovic sent a return of his fierce serve long.
Djokovic managed to fend off one match point earlier in the ninth game while down 5-3, 30-40, executing a deft drop shot that left his Chilean adversary scrambling.
He then held serve to bring the score to 5-4.
In other matches, No. 13 Lorenzo Musetti bounced back from a rocky start to beat Jiri Lehecka 1-6, 7-5, 6-2, setting the stage for an exciting clash with fellow Italian Matteo Berrettini, who triumphed over top seed Alexander Zverev.
Daniil Medvedev progressed past Alexandre Muller with a score of 7-6 (6), 5-7, 6-2, while fourth-seeded Casper Ruud comfortably defeated Roberto Bautista Agut 6-2, 6-1.
In a poignant moment, the 38-year-old French players Richard Gasquet and Gael Monfils were both eliminated, falling to Daniel Altmaier and seventh-seed Andrey Rublev, respectively.
The Monte Carlo Masters marks the beginning of the prestigious clay-court season on the ATP Tour.
