Novak Djokovic and Marin Cilic Make History at Shanghai Rolex Masters 2025

When Novak Djokovic and Marin Cilic took the court in the second round of the Shanghai Rolex Masters Friday, they collectively entered the history books. The matchup officially became the oldest Masters 1000 match ever played, with a combined age of 75 years and 139 days.

Playing their 22nd match against each other, both men, long past their peak and edging closer to retirement, still managed to produce a contest with more fireworks than many had expected.

How the Match Unfolded

Both players started strong on serve, holding comfortably and offering few chances to break. To the surprise of many, Cilic hung in impressively and was actually the first, and only, player in the opening set to generate break points, doing so in the 11th game.

Using his slice backhand and powerful forehand brilliantly, the Croatian matched Djokovic for much of the set. However, once the set reached a tiebreak, it was one-way traffic: Djokovic switched into his patented lockdown mode, closing it out with authority.

Seizing the momentum, the Serbian broke early in the second set, which ultimately proved decisive. While Cilic continued to fight valiantly until the final ball, the set and a break deficit was too much to overcome. Djokovic sealed a 7-6 6-4 victory to move into the third round, where he will face Germany’s Yannick Hanfmann.

Djokovic’s Search for a Big Title in 2025

The 2025 season is on course to be Djokovic’s first since 2017 without a big title. With his schedule unlikely to include the Paris Rolex Masters or the Nitto ATP Finals, Shanghai could very well be his last chance to claim a big trophy this year.

Nevertheless, his season has been remarkable considering his age and physical setbacks. Djokovic reached the semifinals at all four Majors, finished runner-up in Miami, and won the ATP 250 title in Geneva.

His biggest challenges in 2025 have been Carlos Alcaraz and Jannik Sinner, who defeated him in three of the four Majors. After the US Open, Djokovic himself admitted that his best chances might come in best-of-three tournaments like Shanghai, where he is projected to meet Sinner in the semifinals.

He reaffirmed that stance before this tournament, telling reporters, “The Masters events are played over almost two weeks. That’s where I feel I have a better chance, you know, to win a trophy or to make a significant result.”
With Alcaraz withdrawing from the tournament, fans are hoping for another high-stakes showdown between the current hard-court king, Jannik Sinner, and the greatest hard-court player of all time, Novak Djokovic. At this stage of Djokovic’s career, every such matchup feels like it could be the last, and that makes the prospect even more thrilling.