Tabilo stuns Djokovic for second time as Serb’s 100th title bid falters; Alcaraz powers into third round.
Novak Djokovic’s quest for a landmark 100th ATP title hit another painful bump on Wednesday, as the world number one suffered a stunning straight-sets defeat to Chile’s Alejandro Tabilo in the second round of the Monte Carlo Masters.
The 24-time Grand Slam champion delivered a dismal performance littered with 29 unforced errors, crashing out 6-3 6-4 in just his opening match. For Djokovic, this marks a second successive missed opportunity to reach his century of tour-level titles, following his surprise loss to Jakub Mensik in the Miami final.
“This was horrible,” the 37-year-old admitted after the loss. “I didn’t expect to play this badly. It’s a horrible feeling, just sorry for the people who had to witness this.”
It was Djokovic’s 18th appearance in Monte Carlo—a tournament where he triumphed in 2013 and 2015—and no player in the Open era has featured in the event more. But from the moment he surrendered a break advantage in the first set, there was little sign of the resilience that has long defined his career.
World number 32 Tabilo had already toppled Djokovic on clay last year in Rome and once again outplayed the Serbian great. After being broken in the opening game, the 27-year-old Chilean hit back with two breaks of his own to claim the first set. The second followed a similar pattern, with Djokovic handing Tabilo a break in the third game, then failing to convert two crucial break points late in the match. Tabilo eventually sealed the biggest win of his season on his second match point.
Set to face Grigor Dimitrov next, Tabilo reflected: “It has been a tough year, so a little bit of the nerves were there. But I remembered what worked last time, and thankfully, I served well today. It was an unreal match.”
For Djokovic, this latest exit deepens concerns as he enters the critical clay-court stretch ahead of Roland Garros. He remains stuck on 99 career titles, still chasing the elite club that includes only Roger Federer (103) and Jimmy Connors (109).
While Djokovic struggled, Spain’s Carlos Alcaraz made a statement in his return to clay. After a shaky start against Argentina’s Francisco Cerundolo, the world number three roared back to dominate the match 3-6 6-0 6-1. Alcaraz, the reigning French Open champion, won 12 of the final 13 games in a ruthless display.
“I didn’t start well,” Alcaraz admitted. “But I had to do something different—play more aggressively, play my tennis.”
Alcaraz now faces German qualifier Daniel Altmaier in the third round, continuing his preparation to defend his Roland Garros crown. The 21-year-old, who reached the Olympic final on the same surface last year, has now won 13 of his last 14 matches on clay.
Other top seeds also made smooth progress. Norway’s Casper Ruud breezed past Roberto Bautista Agut 6-2 6-1, while Russia’s Andrey Rublev edged past French veteran Gael Monfils in straight sets. Daniil Medvedev overcame a stern test against France’s Alexandre Muller, winning in three sets, and Australia’s Alex de Minaur came from behind to beat Czech Tomas Machac.
British hopeful Jack Draper is set to continue his Monte Carlo campaign on Thursday, when he takes on Alejandro Davidovich Fokina for a place in the quarter-finals. Draper, fresh off his Indian Wells triumph, remains one of the tournament’s in-form threats.
But the spotlight remained firmly on Djokovic’s downfall—a performance he described as “quite a high probability” due to poor preparation. As the clay season heats up, so do the questions surrounding the Serbian legend’s form and fitness.
