Tabilo’s Double Take: Can He Crack the Djokovic Code Again?

Alejandro Tabilo has etched his name into tennis lore by achieving a rare feat: defeating Novak Djokovic not once, but twice. This latest victory at the Monte Carlo Masters has tennis fans buzzing. Can Tabilo continue to challenge the world’s best, or is this just a momentary peak in his career?

The Upset in Monte Carlo

In a stunning second-round upset at the Monte Carlo Masters, Alejandro Tabilo defeated Novak Djokovic 6-3, 6-4. This victory marked Tabilo’s second win against the Serbian superstar, maintaining a perfect record against the 24-time Grand Slam winner. The unseeded Tabilo displayed remarkable composure and skill, continuing his impressive run after overcoming Stan Wawrinka in the first round.

Djokovic, who had a bye into the second round, admitted to a subpar performance, stating, “I expected myself at least to have put in a decent performance. Not like this, it was horrible.” He cited 29 unforced errors as a key factor in his defeat. This loss continues Djokovic’s search for his 100th tour-level title and a record-extending 41st Masters 1000 trophy.

Tabilo, on the other hand, expressed his relief and joy after the match. “It has been a tough year, so a little bit of the nerves were there,” he said in an on-court interview. “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.” This victory is particularly significant for Tabilo, who had a challenging start to the year with a 2-9 win-loss record before turning things around.

The Rome Upset: A Glimpse of Tabilo’s Potential

Tabilo’s first victory over Djokovic came at the 2024 Italian Open in Rome, where he defeated the six-time champion 6-2, 6-3 in the third round. This dominant performance showcased Tabilo’s powerful game and composure under pressure. He broke Djokovic’s serve four times and did not face a single break point himself, securing the win in just 68 minutes.

“[It’s] incredible,” Tabilo said after the match. “I was just trying to keep my nerves in, trying to keep swinging.” This win propelled Tabilo to the fourth round of a Masters 1000 event for only the second time in his career, marking a significant milestone in his burgeoning career.

Djokovic, still seeking his first title of the season at the time, acknowledged his struggles, saying, “I just wasn’t able to find any kind of good feelings on the court, to be honest, with striking the ball. Yeah, I was completely off.”

Who is Alejandro Tabilo?

Alejandro Tabilo Álvarez, born on June 2, 1997, in Toronto, Canada, is a Chilean professional tennis player. Tabilo’s journey in tennis began at a young age, influenced by his older brother, Sebastian. At 13, he moved to Florida to train, and later returned to Santiago, Chile, at 19, determined to follow in the footsteps of Chile’s tennis legends.

Tabilo’s career highlights include:

• ATP Titles: Auckland (2024), Mallorca (2024)
• ATP Challenger Titles: 6
• Career-High Ranking: No. 19 (July 1, 2024)
• Laver Cup Debut: Selected for Team World in 2024
• Grand Slam Debut: Australian Open 2020

Tabilo’s playing style is characterized by his powerful lefty forehand and aggressive baseline game. He idolizes Rafael Nadal and enjoys playing chess, showcasing his strategic thinking both on and off the court.

The Rare Club: Players With Multiple Wins Over Djokovic

Tabilo’s achievement of defeating Novak Djokovic multiple times places him in an exclusive group of players. Very few active players hold a winning record against Djokovic, making Tabilo’s feat even more remarkable.

As of today, April 9, 2025, other active players who have a winning record against Djokovic include:

• Jiri Vesely: 2-0
• Nick Kyrgios: 2-1

Historically, only a handful of players have managed to consistently challenge and defeat Djokovic. Former World No. 1 Andy Roddick, for instance, won five of his nine matches against the Serbian.

Djokovic’s Clay Court Record in 2025

Despite his recent losses, Novak Djokovic remains a formidable force on clay. He has won more than 80% of his tour-level matches on clay and holds 20 clay court titles. However, his performance in 2025 has been inconsistent.

Djokovic’s 2025 season includes:

• Australian Open: Semi-finals (lost to Jannik Sinner)
• Miami Open: Finalist (lost to Jakub Mensik)

Djokovic is aiming to bounce back during the clay season and secure his 100th career title. He will be defending a significant number of points at the French Open, where he is the defending champion.

Tabilo’s Breakthrough Season

The 2024 season marked a significant breakthrough for Alejandro Tabilo. He started the year ranked No. 85 and quickly rose to a career-high of No. 19 after winning his first two ATP singles titles in Auckland and Mallorca. His success extended to Grand Slam tournaments, where he reached the third round at Wimbledon for the first time.

Tabilo’s 2024 highlights include:

• Auckland Champion: First ATP title as a qualifier
• Mallorca Champion: Second ATP title on grass
• Santiago Finalist: Reached the final on home soil
• Rome Masters Semifinals: Defeated Djokovic en route
• Wimbledon Third Round: Best Grand Slam performance to date

His achievements have made him the Chilean and Latin American No. 1, solidifying his position as a rising star in the tennis world.

Can Tabilo Maintain His Momentum?

The question now is whether Alejandro Tabilo can maintain his momentum and continue to challenge the top players in the world. His victories over Djokovic demonstrate his potential, but consistency will be key to his long-term success.

Factors that could contribute to Tabilo’s continued success include:

• Maintaining his aggressive playing style: Tabilo’s powerful forehand and willingness to dictate play have proven effective against top opponents.
• Improving his serve: A consistent and reliable serve will be crucial for holding his own against the best returners in the game.
• Staying mentally strong: Tennis is as much a mental game as it is a physical one. Tabilo’s ability to manage his nerves and stay focused under pressure will be essential.
• Building on his clay-court success: With two wins over Djokovic on clay, Tabilo has shown he can excel on this surface. Continuing to develop his clay-court game could lead to further success in the European clay season.

However, challenges remain:

• Consistency: Tabilo needs to maintain a high level of play consistently, not just in isolated matches against top players.
• Adaptability: Opponents will study his game and look for weaknesses. Tabilo must be able to adapt his strategies and tactics to stay ahead.
• Physical endurance: The demands of the ATP Tour are rigorous. Tabilo needs to stay healthy and maintain his physical conditioning to compete at the highest level week after week.

The Road Ahead

As Alejandro Tabilo continues his journey on the ATP Tour, his recent victories over Novak Djokovic will undoubtedly boost his confidence and attract more attention. Whether he can consistently challenge the top players and win major titles remains to be seen, but his talent and potential are undeniable.

For now, tennis fans will be watching closely to see if Tabilo can continue his remarkable run and establish himself as a force to be reckoned with in the world of tennis.