Alejandro Tabilo now 2-0 against Novak Djokovic after Monte Carlo upset, joins rare company

With a 6-3, 6-4 victory over the legend in Monte Carlo on Wednesday, Alejandro Tabilo improved to 2-0 in his career against Novak Djokovic, having also won their only previous meeting in Rome last year.

With that, the Chilean joins rare company as the ninth player ever to win their first two career meetings against Djokovic, after Roger Federer, Rafael Nadal, Marat Safin, Guillermo Coria, Fernando Verdasco, Nick Kyrgios, Olivier Rochus and Jiri Vesely.

And the company gets even rarer.

Given he also defeated Djokovic in straight sets in their first meeting in Rome, 6-2, 6-3, Tabilo is only the fourth player ever to win their first two career meetings against Djokovic without dropping a set.

Only Nadal, Safin and Kyrgios had previously done that.

Nadal won his first meeting with Djokovic in the 2006 Roland Garros quarterfinals, 6-4, 6-4, retired (after Djokovic had to stop due to a back injury), then beat him 6-2, 7-5 in the 2007 Indian Wells final.

Safin’s the only one to do it in two Grand Slam meetings, defeating him in the first round of the Australian Open in 2005, 6-0, 6-2, 6-1, then in the second round of Wimbledon in 2008, 6-4, 7-6 (3), 6-2.

Kyrgios is the only one to do it in the same year, 2017, and at back-to-back events too, beating him in the quarterfinals of Acapulco, 7-6 (9), 7-5, then in the fourth round of Indian Wells, 6-4, 7-6 (3).

Tabilo is the only one of the group to win his first two meetings with Djokovic in a completed match and without going to a tie-break.

Things were looking encouraging early on for Djokovic on Wednesday, as he broke serve in the very first game of the match, but it would turn out to be his only break of the match—and not only did Tabilo break right back in the next game, but he would then grab one more per set.

At the end of the day, Tabilo was just too solid, finishing the match with an even differential of 16 winners to 16 unforced errors.

Meanwhile, Djokovic was deep into the negatives with 18 winners to 29 unforced errors, with his forehand accounting for that entire deficit—he had six winners to 18 unforced errors on that wing alone.

"Horrible feeling to play this way, and just sorry for all the people that have to witness this," a disappointed Djokovic said afterwards.

For Tabilo, though, it's been a welcome return to form—after a career year in 2024 highlighted by his first two ATP titles, his first Masters 1000 semifinal in Rome and cracking the Top 20 in the summer, he came into Monte Carlo this week ranked No. 32 after a 2-9 start to 2025.

"It's been a tough year, so a little bit of the nerves were there, but I just tried to remember what I did well against him last time," the 6' 2" lefty said afterwards. "I served well today, which helped me to regroup my game after that first game, and it was an unreal match, I think.

"Match by match I've been getting better, and I'm so happy."

Awaiting Tabilo in the third round will be Grigor Dimitrov, a 4-6, 6-3, 6-1 winner over Monegasque wild card Valentin Vacherot later in the day.

To flip the 2-0 script the other way, Dimitrov has beaten Tabilo in both of their previous meetings, though the first of those could have gone either way—he was two points from losing in the second round of Miami last year, down a set and down 5-3 in the second set tie-break, but battled back to defeat the Chilean, 6-7 (5), 7-6 (5), 6-2.

The Bulgarian then won again at Laver Cup last fall, 7-6 (4), 7-6 (2).