The sun-drenched courts of Monte Carlo, typically a stage for Novak Djokovic’s relentless brilliance, bore witness to an unsettling spectacle at the 2025 Masters. The Serbian legend, a 24-time Grand Slam champion, exited in the second round, toppled 6-3, 6-4 by Chile’s Alejandro Tabilo in a performance that left fans and Djokovic himself grasping for answers. Something was undeniably off, and the echoes of his frustration lingered long after the final point.
Djokovic, now 37, stepped onto the clay of Court Rainier III chasing his 100th career title, a milestone that would place him alongside Jimmy Connors and Roger Federer. Yet, from the outset, the Serbian seemed a shadow of his usual self. His trademark precision faltered, with 29 unforced errors piling up against just 18 winners. Tabilo, ranked world No. 32, capitalized ruthlessly, breaking Djokovic three times in a match that lasted under 90 minutes. For the second time in 11 months—following a similar upset in Rome—the Chilean had Djokovic’s number, joining an elite trio with Marat Safin and Jiri Vesely as players who’ve faced him multiple times without a loss.
“I expected myself at least to have put in a decent performance. Not like this, it was horrible,” Djokovic admitted afterward, his voice heavy with disappointment. “I was hoping it was not going to happen, but it was quite a high probability I’m going to play this way.” The words revealed a rare vulnerability, a crack in the armor of a player who has long bent the sport to his will. His return, often hailed as the best in men’s tennis history, betrayed him, with shots landing short and lacking depth. Tabilo, by contrast, was clinical, winning 81 percent of first-serve points and keeping Djokovic on the defensive. “I just tried to remember what I did well last time,” Tabilo said courtside. “Thankfully I served well today and it helped me a lot. It was an unreal match.”
The defeat wasn’t just a blip—it hinted at deeper struggles. Djokovic’s 2025 season has been uneven by his lofty standards, with a 12-6 record and no titles since the 2023 ATP Finals. A Miami Open final loss to teenager Jakub Mensik, hampered by a viral infection, had already raised eyebrows. In Monte Carlo, whispers of physical woes surfaced again. While Djokovic dismissed concerns about his eye or arm, saying, “There’s no injury. It’s all good,” his body language told a different story. The clay, a surface he’s conquered twice at Roland Garros, seemed to sap his rhythm, a stark contrast to his Olympic gold triumph on the same surface in 2024.
Monte Carlo has rarely been kind to Djokovic in recent years. Since his titles in 2013 and 2015, he’s failed to reach the quarter-finals in five of his last six appearances. Yet, this loss stung more, coming against a player who arrived with a 2-9 record in 2025 and an eight-match clay losing streak. “I don’t know. I don’t have it,” Djokovic said when pressed for an explanation, a candid admission that underscored his bewilderment. His focus, he insisted, remains singular: “Roland Garros. That’s it.” The French Open, starting May 25, looms as his chance to reclaim supremacy, but this stumble has cast doubt on his clay-court readiness.
The match unfolded under Monaco’s azure skies, with Djokovic breaking Tabilo in the opening game, a fleeting glimpse of his old fire. But Tabilo roared back, breaking twice to claim the first set. In the second, a single break in the third game proved decisive, as Djokovic’s errors mounted and his returns faltered. Tabilo, sensing blood, saved two break points late to seal the upset, his second career-defining win over the Serbian. “I was ready for him to come out and almost want to kill me,” Tabilo later said, revealing his game plan to stay aggressive and exploit Djokovic’s discomfort.
For fans, the sight of Djokovic unraveling was jarring. Social media buzzed with concern, some speculating about age catching up, others pointing to the absence of new coach Andy Murray, with brother Marko filling in. Yet, Djokovic’s resolve remains. His Miami run, where he found “joy on the court,” suggests the fire still burns. Monte Carlo, though, was a stark reminder of mortality, even for a player who’s defied it for two decades. As Tabilo advances to face Grigor Dimitrov, Djokovic’s path now leads to Madrid, where he’ll seek to rediscover the spark that’s carried him to 99 titles—and counting.