In 2013, Novak Djokovic finally conquered the Monte Carlo Open, a tournament that had long eluded him due to two painful final losses to Rafael Nadal in 2009 and 2012. That victory shattered Nadal’s extraordinary 46-match winning streak at the event. Two years later, Djokovic returned and clinched a second title, making history as the first player to win the season’s opening three ATP Masters 1000 tournaments. Since then, he’s added 47 more titles to his collection — including an Olympic gold medal in Paris in 2024 — bringing his career tally to 99.
So when Djokovic stepped onto Monte Carlo’s clay courts this year, fans and analysts alike buzzed with excitement over the possibility of him reaching his milestone 100th title. But tennis, known for its unpredictability, threw a wrench into that dream.
DID YOU KNOW❓
With a 6-2 6-3 win in Rome last May and a 6-3 6-4 win in Monte Carlo today, 🇨🇱 Alejandro Tabilo is just the fourth man EVER to win his first two meetings with Djokovic without losing a set. 💥💥
The other three? Nadal, Safin and Kyrgios:https://t.co/qBpbOahm5S
— TENNIS (@Tennis) April 9, 2025
On Wednesday, Chile’s Alejandro Tabilo pulled off a massive upset, toppling the 24-time Grand Slam winner in straight sets, 6-3, 6-4. Djokovic looked off-form, committing 29 unforced errors and lacking rhythm in what was a flat start to his clay season. The defeat wasn’t just a personal disappointment for Djokovic; it also connected Tabilo to a remarkable record involving Rafael Nadal — a connection that certainly wasn’t welcome news for the Serbian legend.
According to Tennis.com, Tabilo is now just the fourth player in history to win his first two matches against Djokovic without dropping a set. The only others to achieve this rare feat are Nadal, Marat Safin, and Nick Kyrgios. Tabilo’s previous win came at the Rome Masters in May 2024, where he won 6-2, 6-3. Now, with this victory in Monte Carlo, he stands among elite company.
Each of the players who accomplished this did it in different ways. Nadal’s wins came early in his career, in 2006 and 2007. Safin managed it at two Grand Slams — the Australian Open and Wimbledon. Kyrgios did it in back-to-back hard court tournaments in 2017. Tabilo, now, is the only one to do it in two completed matches without needing a tiebreaker.
Even more astonishing, Tabilo is now one of just nine players to hold a 2-0 head-to-head record against Djokovic, joining the likes of Roger Federer, Rafael Nadal, Marat Safin, Guillermo Coria, Fernando Verdasco, Nick Kyrgios, Olivier Rochus, and Jiri Vesely.
Djokovic was brutally honest about his poor performance afterward. Reflecting on the loss, he called it “horrible,” and admitted he had expected a tough match but didn’t foresee playing this badly. He apologized to the fans, expressing his disappointment in not being able to deliver a decent showing.
With Monte Carlo behind him, Djokovic now turns his attention to the Madrid Open. He will be joined by Andy Murray in his corner, aiming to reset and build momentum ahead of his primary clay-court goal — winning Roland Garros. Whether the loss exposed deep-seated problems or was just an off-day remains up for debate. But one thing is certain: Djokovic’s journey to his 100th title will be a dramatic, closely watched chapter in tennis history.