In a stunning upset that sent shockwaves through the tennis world, world number five Novak Djokovic crashed out of the Monte Carlo Masters in his opening match on Wednesday, falling in straight sets to Chile’s Alejandro Tabilo. The 6-3, 6-4 defeat not only marks a disappointing start to Djokovic’s clay season but also extends his title drought since winning gold at the Paris Olympics last year.

Djokovic, 37, who had entered the tournament dealing with the effects of an eye infection picked up in Miami, struggled visibly with rhythm and intensity. Despite saying he didn’t have “very high expectations” for Monte Carlo, the Serbian star admitted he had not anticipated such a poor performance. “It was actually more like the worst day (at the office)... just horrible,” Djokovic said. “I expected myself at least to have put a decent performance. Not like this.”

Tabilo, ranked 32nd in the world, took full advantage of Djokovic’s erratic form, facing little resistance as he notched his second straight clay win over the 24-time Grand Slam champion—having previously defeated him at the 2023 Italian Open. The Chilean now advances to face Grigor Dimitrov in the round of 16. Despite the early exit, Djokovic maintained that his primary goal remains the French Open, set to begin later this spring. He also confirmed his participation in the Madrid Open, which he will contest for the first time since 2022.

Alcaraz Dominates After Shaky Start

While Djokovic’s clay season began with a jolt, world number three Carlos Alcaraz made a triumphant return to the red dirt. The Spanish sensation rallied back from a set down to defeat Argentina’s Francisco Cerundolo 3-6, 6-0, 6-1 in emphatic style, securing his first-ever win at the Monte Carlo Masters.

The 21-year-old had a rocky start, dropping four consecutive games in the first set and appearing out of sync. But Alcaraz quickly found his rhythm, adjusting his strategy and taking control of the match. “I just knew that I had to do something else, play more aggressively, and play my own tennis,” Alcaraz said post-match. “The most important change was the return... I tried to return closer to the line and push him.”

He will face Germany’s Daniel Altmaier, ranked 84th, in the round of 16. Altmaier defeated veteran Frenchman Richard Gasquet in a three-set battle. Gasquet, who received a warm send-off from fans, confirmed he will retire following the French Open, bringing the curtain down on a career that spanned over two decades. “I started with Agassi and I’ll finish with Alcaraz,” said Gasquet, reflecting on the generational shift in tennis.

Other Highlights from Monte Carlo

• Casper Ruud, last year’s finalist and current fourth seed, eased past Roberto Bautista Agut with a commanding 6-2, 6-1 win.

• Andrey Rublev, the defending Monte Carlo champion, dispatched Gael Monfils in straight sets.

• Daniil Medvedev, Alex de Minaur, Arthur Fils, and Lorenzo Musetti also advanced to the next round with strong performances.

With Djokovic’s early exit and Alcaraz's surge, the tournament is wide open as the clay season heats up. As newer stars step up and veterans prepare for their swan songs, Monte Carlo continues to be a stage for both transition and transformation in men’s tennis.