Novak Djokovic’s wait for his 100th ATP singles title continues after the two-time champion exited the Monte Carlo Masters in a straight-set opening loss to Alejandro Tabilo.
Djokovic, 37, made 29 unforced errors compared to his 18 winners in a subdued start to his clay-court season, which ended in a 6-3 6-4 defeat.
The record 24-time men’s major champion had won the last 10 matches he had contested on clay – including his run to Olympic gold in July.
But Chilean Tabilo, the last player to beat Djokovic on the surface at the Italian Open 11 months ago, replicated that surprise victory to reach the third round.
Earlier on Wednesday, Carlos Alcaraz rallied to a comeback victory over Francisco Cerundolo in the 21-year-old’s first clay match of the season.
The Spanish world number three was unable to match Argentine Cerundolo in the first set but dominated thereafter, winning 12 of the last 13 games in a 3-6 6-0 6-1 win.
Norwegian fourth seed Casper Ruud beat Spain’s Roberto Bautista Agut 6-2 6-1, while Russian seventh seed Andrey Rublev overcame Frenchman Gael Monfils 6-4 7-6 (7-2).
Great Britain’s Jack Draper is back in action on Thursday, when the Indian Wells champion faces Spain’s Alejandro Davidovich Fokina for a quarter-final place.
Djokovic’s wait for century goes on
Djokovic is aiming to become only the third man in the Open era to win 100 Tour-level titles, having reached 99 by completing a career ‘Golden Slam’ at the Paris 2024 Olympics.
But, after being stunned by Czech teenager Jakub Mensik in the Miami Open final in his previous attempt at reaching the landmark, that wait goes on.
Making his 18th appearance in Monte Carlo, 2013 and 2015 champion Djokovic made the perfect start by breaking Tabilo’s serve in the opening game.
But world number 32 Tabilo once again had the measure of the former world number one, against whom he has now achieved the two biggest wins of his career.
The 27-year-old produced an excellent response following his early setback, twice breaking an out-of-sorts Djokovic to turn the first set around.
Tabilo then struck what proved the decisive blow in the third game of set two, with Djokovic conceding on a second break point after inviting pressure with costly errors.
The Serb attempted to hang on but Tabilo saved two break points to move within one game of victory, before sealing it on his second match point.
He will face Bulgarian 15th seed Grigor Dimitrov or wildcard Valentin Vacherot next.