Old Master at it again! Novak Djokovic sets new record with second-round win at Shanghai Masters 2025

Novak Djokovic is a four-time champion at Shanghai Masters.

The tennis legend Novak Djokovic continues to defy the march of time, etching his name into the history books once again at the Shanghai Masters 2025.

Djokovic, a record four-time champion in Shanghai, progressed to the third round in style after defeating long-time rival and former Grand Slam champion Marin Cilic in straight sets.

A 24-time Grand Slam winner himself, this is Djokovic’s first event since the heartbreaking semi-final loss to Carlos Alcaraz at US Open in the first week of September.

At 38, the Serbian has only participated in a handful of tournaments season, winning one title—the ATP 250 Geneva Open, which was a landmark 100th title, putting Djokovic in the company of Roger Federer and Jimmy Connors as the only male tennis players to win 100 or more titles on ATP tour.

On Friday, Djokovic added another record to him name. By beating Cilic, he has now become the oldest player to defeat a Grand Slam champion at ATP Masters 1000 events since the format’s introduction in 1990.

1 – Since the format's introduction in 1990, Novak Djokovic (38y 133d) is now the oldest player to defeat a Grand Slam champion at an ATP Masters 1000 event. Eternal.#RolexShanghaiMasters | @SH_RolexMasters @atptour @ATPMediaInfo pic.twitter.com/Xl0ZWKxjBL

— OptaAce (@OptaAce) October 3, 2025

At 38 years and 133 days old, Djokovic defeated the 37-year-old Croatian 7-6 (7-2), 6-4. The match itself was historic—the combined age of the two veterans (75 years and 139 days) set a new record for the oldest ATP Masters 1000 main draw match ever played.

This win also marked Djokovic’s 20th victory over Cilic in their 22 career meetings.

Shanghai holds a special place in Djokovic’s illustrious resume. At the Shanghai Masters, where he has already lifted the trophy four times, the Serbian great added another milestone by securing his 40th career match win at the tournament.

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With this achievement, he became the first male player in history to record at least 40 match wins at six different ATP Masters 1000 events.

4-time champ reaches win no. 40 in Shanghai 🎖️Djokovic makes it 20-2 vs Cilic after defeating him 7-6 6-4, yet to lose a match before QFs here!@DjokerNole #RolexShanghaiMasters pic.twitter.com/i5RlewGv8o

— Rolex Shanghai Masters (@SH_RolexMasters) October 3, 2025

Novak Djokovic’s US Open 2025 campaign was also a historic one, even though he didn’t lift the trophy. At 38 years and 103 days old, he became the oldest man in the Open Era to reach the semi-finals of all four Grand Slams in a single season.

His dream of clinching a record-breaking 25th Grand Slam title faded at Flushing Meadows, where his run came to an end in the semi-finals against Carlos Alcaraz, who defeated him in straight sets (6-4, 7-6(4), 6-2).

In 2025 so far, Djokovic’s sole title win came at the Geneva Open, where he defeated Hubert Hurkacz in the final. It was his 100th career ATP Tour singles title, making him only the third man in the Open Era to reach this milestone, joining Jimmy Connors (109) and Roger Federer (103).

He also became the first player to win at least one ATP singles title in 20 consecutive seasons. Then, at 38 years and 2 days old, Djokovic became the third-oldest man to win an ATP Tour singles title in the Open Era.

Next, the 38-year-old will take on German qualifier Yannick Hanfmann in the third round at the Shanghai Masters.

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