In a stunning upset under the Mediterranean sun on April 9, 2025, Novak Djokovic, the 24-time Grand Slam champion, suffered a rare and humbling defeat at the Monte Carlo Masters. The Serbian legend, ranked No. 5 in the world, fell in straight sets to Chile’s Alejandro Tabilo, a tenacious left-hander who turned the clay courts of Monaco into his personal stage. The final scoreline read 6-3, 6-4, a result that ended Djokovic’s hopes of capturing his 100th career title—at least for now—and handed Tabilo his second consecutive victory over the tennis titan on clay, all without dropping a single set.
The match, which unfolded on the prestigious Court Rainier III, began with an air of unease for Djokovic. Fresh off a first-round bye and entering his first clay-court event since clinching Olympic gold in Paris last year, the 37-year-old appeared out of sync from the opening exchanges. Tabilo, ranked No. 32, pounced early, breaking Djokovic’s serve in the very first game with a blend of aggressive groundstrokes and clever movement. “I just wasn’t able to find any kind of good feelings on the court, striking the ball,” Djokovic later confessed, his frustration palpable as he reflected on a performance riddled with 29 unforced errors. For a player renowned for his precision and adaptability, this was a startling lapse.
Tabilo, by contrast, was a picture of composure and confidence. The 27-year-old Chilean, who had already toppled three-time Grand Slam champion Stan Wawrinka in a grueling three-setter the day before, showed no signs of fatigue. His left-handed spin and fearless shot-making kept Djokovic off balance, particularly on the backhand side, where the Serb’s usually reliable wing faltered repeatedly. “I came on court just looking around, trying to soak it all in,” Tabilo said afterward, his voice tinged with disbelief as he processed the magnitude of his achievement. “I’m trying to wake up right now.” For him, this wasn’t just a win—it was a dream unfolding in real time.
The first set slipped away from Djokovic in just over 30 minutes, a 6-3 deficit that hinted at deeper troubles. Fans who’d hoped for a trademark comeback were left wanting. In the second set, Tabilo broke early again, capitalizing on a Djokovic double fault—a recurring theme in a match where the Serb’s serve betrayed him five times. Though Djokovic briefly rallied, clawing back a break to level the set at 4-4, his resurgence was short-lived. Tabilo held firm, sealing the match with a powerful forehand that Djokovic could only watch sail past. The crowd, initially buzzing with anticipation for their beloved “Nole,” fell into a stunned silence, then erupted in applause for the underdog’s heroics.
This defeat marks a rare blemish in Djokovic’s storied career at Monte Carlo, where he’s lifted the trophy twice before, in 2013 and 2015. It’s also a continuation of an unexpected narrative: Tabilo now boasts a 2-0 head-to-head record against him, both wins coming on clay, the surface where Djokovic has historically thrived with 20 titles. Their first clash, a 6-2, 6-3 drubbing in Rome last year, had been an anomaly—or so it seemed. Now, with this second straight-sets triumph, Tabilo has firmly established himself as Djokovic’s kryptonite, a player who somehow unlocks the Serb’s vulnerabilities when the stakes are high.
For Djokovic, the loss stings beyond the scoreline. Coming off a 12-5 season that included a final in Miami and a semifinal run at the Australian Open, he’d arrived in Monte Carlo eager to kickstart his clay campaign and inch closer to that elusive 100th title. Instead, he exits in the second round, his earliest departure from the tournament since 2011, when he withdrew before his third match. “Completely off,” he described his play, a candid admission from a champion unaccustomed to such struggles. The setback raises questions about his form as the French Open looms, a tournament he’s won three times, including last year, and where he’ll defend his crown next month.
Tabilo, meanwhile, marches into the Round of 16, where he’ll face either Grigor Dimitrov or Valentin Vacherot. His season, which began with a dismal 3-9 record, is suddenly alight with possibility. Beating Wawrinka and Djokovic back-to-back—two former Monte Carlo champions—has catapulted him into the spotlight, his gritty resolve and silky shot-making earning admiration across the tennis world. “It’s crazy,” he marveled, still grappling with the reality of toppling one of the sport’s all-time greats. For now, the Chilean is living a fairytale in Monaco, while Djokovic retreats to regroup, his quest for triple-digit glory delayed but far from derailed.