The 100th ATP singles title is still eluding Novak Djokovic. He has come close on a couple of occasions this season, but while a muscle tear ended his campaign in the Australian Open semifinal, a stunning upset at the ends of a 19-year-old Jakub Mensik in the Miami open final ensured the Serb’s tite drought stretched even further. To accomplish the magical number of 100, Nole is now set to begin another campaign – but this time on clay. The 24-time GS winner will take on his Chilean opponent Alejandro Tabilo on Wednesday in R32 of the Monte Carlo Masters. Who’s likely to have the last laugh in this face-off? Let’s find out.

Novak Djokovic vs Alejandro Tabilo: Preview

Novak Djokovic has been mostly inconsistent in the 2025 season. Back in January, he started the season with a QF appearance in Brisbane before losing to American Reilly Opelka. Then in Melbourne, he was looking in great form, but after sustaining an injury in the quarterfinal match against Carlos Alcaraz – a match he eventually completed and won, Djokovic was forced to withdraw from the semis against Alexander Zverev after losing the first set.

He went on a recovery break for a month, but when he returned, the Serb failed to impress. In Doha, Italy’s Matteo Berrettini ousted him in his first match itself with a score line of 7-6(4), 6-2. And his poor run continued in the Indian Wells, too, where Dutchman Botic Van de Zandschulp eliminated him in R64.

Luckily, the Miami Open brought some relief for the former World No.1, as he succeeded in making it to the final, but only to be toppled by the teenage sensation Jakub Mensik. The latter broke Djokovic’s dream to lift the 100th ATP trophy and won the final with a scoreline of 7-6(4), 7-6(4).

Djokovic’s opponent, Alejandro Tabilo, on the flipside, has had a forgettable season to say the best. He started with the Brisbane International, where he was ousted early in R32. Then at the ASB Classic, too, his fate remained unchanged. Tabilo crashed out in R16 with a loss against American Nishesh Basavareddy.

The Chilean kept witnessing early exits in subsequent events, including the Australian Open, Argentina Open, Rio Open, and Chile Open, where he was eliminated in the first round, R16, R32, and R16, respectively.

At the Indian Wells, Tabilo managed to win his opening encounter against Serbian Dušan Lajović. However, he couldn’t move past R32 after losing to Taylor Fritz. Similarly, in Miami, he won the R64 match against Corentin Moutet, but got eliminated in the next round, losing to Casper Ruud. In his last appearance at the US Men’s Clay Court Championships in Houston, Tabilo crashed out in the R16 against eventual winner Jenson Brooksby.

Djokovic v Tabilo: Head-to-Head

Novak Djokovic and Alejandro Tabilo have faced each other only once on the Tour so far. And it’s Tabilo who’s currently leading the h2h tally 1-0 against the Serbian.

• 2024 Italian Open R32: Tabilo 6-2, 6-3

Prediction: Novak Djokovic to win in straight sets

While he hasn’t really shined consistently on the court this season, Novak Djokovic still has a singles record of 12-5 in 2025, which is far better than Alejandro Tabilo’s 3-9. When it comes to event history, this will be Djokovic’s 18th Monte Carlo Masters campaign. Most by any ATP player. He’s been a former champion as well. The Serbian lifted the trophy here back in 2013 and 2015. In the Monte Carlo Masters, Djokovic has a reasonable 39-15 win-loss record. But what about his recent appearances at the event? Well, in the last three editions (2022, 2023, and 2024), he finished in R32, R16, and the SF, respectively.

On the other hand, Tabilo made his Monte Carlo Masters debut last season. After winning his opening match, he failed to move ahead, losing to Casper Ruud in R32.

Speaking of their playing styles, Djokovic is generally famous for his counter-attacks and aggressive strokes. He’s got amazing court coverage ability as well. In short, his baseline performance is equally as good as his net game. Tabilo, on the other hand, is an all-court player with a strong serve and an effective baseline game. He can also stun his opponents with drop shots. Not to mention his powerful two-handed backhand as well.

While Tabilo might be ahead in the h2h tally as of now, his recent form doesn’t suggest he will be able to pose a challenge to the Serbian. The prediction is for Novak Djokovic to win the match in straight sets and advance.