Novak Djokovic’s pursuit of his 100th career title met with yet another unexpected setback, this time at the hands of a familiar opponent.
Alejandro Tabilo, who previously shocked the 24-time Grand Slam champion at last year’s Italian Open, triumphed over Djokovic with a score of 6-3, 6-4 in the second round of the Monte Carlo Masters.
Returning to clay, Djokovic shared after the match that he had kept his expectations in check.
“Today was honestly one of my worst days on the court. I hoped it wouldn’t go this way, but deep down, I knew the likelihood was high that I would perform like this. I just don’t know what happened,” he admitted.
“It was dreadful. Playing at this level leaves a horrible feeling; I sincerely apologise to everyone who had to watch that.”

Novak Djokovic suffers defeat in Monte Carlo. Getty
“I expected to at least put in a satisfactory performance, but this was just unacceptable. It has been dreadful.”
“To be honest, my expectations were low; I was aware I was up against a tough competitor, and I anticipated a challenging match… but I honestly didn’t foresee it being this bad”.
Tabilo sealed his victory with his second match point when Djokovic’s return sailed long after a strong serve.
Djokovic managed to fend off one match point in the ninth game while trailing 5-3 and 30-40 on his serve. He executed a clever drop shot that Tabilo failed to reach.
The Serb, who recently lost the Miami Open final to Jakub Mensik, will turn 38 next month, shortly ahead of the French Open starting on May 25.
Defending French Open champion Carlos Alcaraz commenced his clay season with a comeback victory, defeating Francisco Cerundolo 3-6, 6-0, 6-1 in the second round.
Second-seeded Alcaraz came off a surprising loss to Belgian veteran David Goffin in his first outing at the Miami Open.
Another upset appeared imminent when Cerundolo, ranked No. 22, claimed the first set, but Alcaraz regained control and converted five out of seven break points in the second and third sets.

Alejandro Tabilo of Chile shakes hands with Djokovic of Serbia at the net after his victory in the Men’s Singles Second Round match on day four of the Rolex Monte-Carlo Masters at Monte-Carlo Country Club on April 09, 2025 in Monte-Carlo, Monaco. (Photo by Clive Brunskill/Getty Images) Getty
Alcaraz aims to secure his second title of 2025 and sharpen his clay-court skills ahead of his title defence at Roland Garros next month.
In other results, 13th seed Lorenzo Musetti defeated Jiri Lehecka 1-6, 7-5, 6-2, setting up a last-16 encounter with compatriot Matteo Berrettini, who advanced by overcoming top seed Alexander Zverev on Tuesday.
Daniil Medvedev triumphed over Alexandre Muller 7-6 (6), 5-7, 6-2, while fourth seed Casper Ruud dispatched Roberto Bautista Agut with a score of 6-2, 6-1.
Veteran Frenchmen Richard Gasquet and Gael Monfils, both aged 38, faced elimination at the hands of Daniel Altmaier and seventh seed Andrey Rublev respectively.
The Monte Carlo Masters marks the inaugural major clay-court tournament of the ATP Tour calendar.
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