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The Chilean benefitted from a below-par performance from Djokovic and held his nerve in the critical moments to earn a standout 6-3, 6-4 second-round win in The Principality.

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 Italian ATP Masters 1000 event. In their second meeting, Tabilo once again proved too strong for the Serbian, who struggled to find his range from the baseline and cope with Tabilo’s flat ball-striking.

"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."

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

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.

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 ATP Rankings for the first time in two years, is chasing his first title since he won on clay in Rome in 2023.

Another Australian, Alexei Popyrin, fought back from a set down to beat Frances Tiafoe 3-6 6-3 6-3. 

The 25 year-old will meet fourth seed Casper Ruud in the round of 16.