Tabilo upsets Djokovic in Monte-Carlo, maintains perfect record against the Serbian

Alejandro Tabilo maintained his perfect record against Novak Djokovic on Wednesday at the Rolex Monte-Carlo Masters, where he stunned the Serbian for the second time in a year.

The Chilean benefitted from a below-par performance from Djokovic to earn a standout 6-3, 6-4, 88-minute second-round win in The Principality.

“It has been a tough year, so a little bit of the nerves were there,” said Tabilo, who has now earned four Top 20 wins. “I remembered last time what I did well and thankfully I served well today and it helped me a lot. It was an unreal match.”

Djokovic’s previous clay-court defeat came against Tabilo in Rome last season, when the 27-year-old dropped just five games to advance at the Masters 1000. Meeting for the second time, Tabilo once again proved too strong for the Serbian, who struggled to find his range from the baseline and cope with Tabilo’s flat ballstriking.

Having also defeated former champion Stan Wawrinka in the first round, Tabilo has recorded consecutive tour-level wins for the first time since last August, when he reached the third round in Montreal. His best result at a Masters 1000 event came in Rome last year, when he advanced to the semi-finals.

Alejandro Tabilo.

Soak it all in ✨#RolexMonteCarloMasters pic.twitter.com/yB5h0l9kM9

— Rolex Monte-Carlo Masters (@ROLEXMCMASTERS) April 9, 2025

Djokovic reached the final in Miami last month, falling agonisingly short of his 100th tour-level title.  The 37-year-old, a two-time champion in Monte-Carlo, struggled with his balance and committed 14 unforced errors in the first set in his first match on clay since he won the gold medal at the Paris Olympics. He was unable to hit through Tabilo in the second set and squandered his only break point chances of the set in the eighth game.

The former No. 1 in the PIF ATP Rankings will next head to the ATP Masters 1000 event in Madrid, where he is expected to be joined again by coach Andy Murray, who was absent from the third seed’s box this week.

In other action, eighth seed Alex de Minaur began his campaign with a 3-6, 6-0, 6-3 win against Tomas Machac. The Australian, who reached the quarter-finals last year, is chasing his first title of the season. He will play Daniil Medvedev next and could meet Tabilo in the quarter-finals.

Tabilo takes on Grigor Dimitrov in third round after the Bulgarian survived a scare from Monegasque wild card Valentin Vacherot. After dropping the first set, Dimitrov responded to earn a 4-6, 6-3, 6-1 win.

Ninth seed Medvedev advanced past Frenchman Alexandre Muller in a topsy-turvy two-hour, 50-minute clash. Medvedev failed to convert from 5-3 in the second set, eventually prevailing in the decider to triumph 7-6(6), 5-7, 6-2. Medvedev, who is competing outside the Top 10 in the PIF ATP Rankings for the first time in two years, is chasing his first title since he won on clay in Rome in 2023.

Did You Know?
Tabilo is just the third player to have faced Djokovic at least twice and not lost, joining Marat Safin and Jiri Vesely