In a stunning turn of events, Novak Djokovic's quest for a historic 100th career title came to an abrupt halt as he faced another surprising defeat at the Monte Carlo Masters. This time, it was Alejandro Tabilo who delivered the blow, triumphing 6-3, 6-4 in the second round.

Tabilo, the 27-year-old Chilean, reminisced about his previous victory over Djokovic at last year’s Italian Open. "It was an unreal match," he said, crediting his solid serving and mental toughness for the win. He secured the match on his second point after Djokovic mishit a return, marking a remarkable 2-0 record against the acclaimed 24-time Grand Slam champion.

With this loss, Djokovic joins the ranks of only a few players—like Marat Safin and Jiri Vesely—who have managed to beat the Serbian twice without tasting defeat.

The stakes were high for Djokovic, who aimed to become the only player to win each Masters event at least three times. Despite the pressure, he expressed disappointment in his performance, noting a staggering 29 unforced errors. "I was hoping to at least put in a decent performance. But this? It was horrible," Djokovic lamented, revealing the toll the match took on his morale.

As the defending Miami Open champion, Djokovic is feeling the weight of expectations as he approaches his 38th birthday next month and the eagerly anticipated French Open on May 25.

On a brighter note, defending French Open champion Carlos Alcaraz kicked off his clay season with a comeback victory against Francisco Cerundolo. After dropping the first set, the second-seeded Alcaraz rallied to clinch the match 3-6, 6-0, 6-1, dispelling fears following his earlier upset at the Miami Open.

Meanwhile, other notable matches saw Lorenzo Musetti overcoming Jiri Lehecka to set up a third-round clash with fellow Italian Matteo Berrettini, who stunned top seed Alexander Zverev.

As the excitement builds around the Monte Carlo Masters, the tournament signifies the official start of the ATP Tour's clay-court season, with plenty of drama and upsets to keep fans on the edge of their seats.