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Novak Djokovic can answer one big question when he returns to tennis at the Shanghai Masters

Photo by Maddie Meyer/Getty Images
Photo by Maddie Meyer/Getty Images
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Novak Djokovic will be making his return to ATP Tour action sooner than expected.

All signs were pointing towards the 38-year-old skipping the upcoming Shanghai Masters, before he changed his mind last minute.

Returning to the court for the first time since losing in the semifinals of the US Open, Djokovic will play at the Shanghai Masters, where he will compete as the number-four seed.

The Serb has won the event four times previously and finished as runner-up to Jannik Sinner 12 months ago.

Novak Djokovic and Jannik Sinner pose with their trophies after the 2024 Shanghai Masters final
Photo by Lintao Zhang/Getty Images

He’ll be hoping to go one better in 2025 and answer one big question in the process.

Novak Djokovic has a chance to prove he can still beat Carlos Alcaraz and Jannik Sinner in best-of-three

The 24-time Grand Slam champion has played four matches against Sinner and Carlos Alcaraz at Grand Slams this year, losing three.

Running out of steam against his two younger rivals on several occasions this year, the belief seems to be that Djokovic can’t keep up with the pair in best-of-five Grand Slam matches.

Djokovic himself had this to say after losing to Alcaraz in the semifinals of the 2025 US Open.

“Best-of-five makes it very, very difficult for me to play them, particularly if it’s the end stages of the Grand Slam,” he said.

“It will be very difficult for me in the future to overcome the hurdle of [Jannik] Sinner, [Carlos] Alcaraz, in the best-of-five on the Grand Slams. I think I have a better chance in best of three, but in best of five, it’s tough.”

Novak Djokovic reacts during his defeat to Carlos Alcaraz at the 2025 US Open
Photo by Maddie Meyer/Getty Images

Many others agreed with the 38-year-old, including former WTA Finals champion Caroline Garcia, who claimed Djokovic has a better chance in best-of-three.

“When he arrives at the moment to play Alcaraz or Sinner in a best-of-five, he’s unfortunately not able to do it anymore. Maybe in best of three, he can do more things, but in best of five, it looks like he’s struggling this year,” she said.

Travelling to Shanghai, Djokovic may have an opportunity to prove whether or not he can indeed beat Sinner or Alcaraz in a best-of-three set match.

The number one and two seeds are likely to make a deep run at the Shanghai Masters, having both enjoyed remarkably consistent seasons.

If Djokovic can meet either player during the latter stages of the event, he will finally get the chance to secure a rare win.

But how has the Serb performed against Alcaraz and Sinner in best-of-three during his career so far?

Novak Djokovic’s best-of-three record against Carlos Alcaraz and Jannik Sinner

Djokovic has played nine best-of-three set matches against Alcaraz and Sinner, emerging victorious on five occasions.

MatchWinnerLoserScore
2024 Shanghai Masters – FJannik SinnerNovak Djokovic7-6, 6-3
2024 Olympics – FNovak DjokovicCarlos Alcaraz7-6, 7-6
2023 Davis Cup – SFJannik SinnerNovak Djokovic6-2, 2-6, 7-5
2023 ATP Finals – FNovak DjokovicJannik Sinner6-3, 6-3
2023 ATP Finals – SFNovak DjokovicCarlos Alcaraz6-3, 6-2
2023 ATP Finals – RRJannik SinnerNovak Djokovic7-5, 6-7, 7-6
2023 Cincinnati Open – FNovak DjokovicCarlos Alcaraz5-7, 7-6, 7-6
2022 Madrid Open – SFCarlos AlcarazNovak Djokovic6-7, 7-5, 7-6
2021 Monte-Carlo Masters – 2RNovak DjokovicJannik Sinner6-4, 6-2
Novak Djokovic’s best-of-three record against Carlos Alcaraz and Jannik Sinner

His last best-of-three win came in the final of the 2024 Olympic Games, when Djokovic beat Alcaraz in straight sets to secure the gold medal.

Novak Djokovic poses with his Olympic gold medal in 2024
Photo by Clive Brunskill/Getty Images

Perhaps his most impressive best-of-three achievement came in 2023, when he beat Alcaraz and Sinner in back-to-back matches to win a record seventh ATP Finals title.

He may need to do the same if he wants to lift the Shanghai Masters title next month.

Only time will tell if Djokovic can beat either Sinner or Alcaraz in Shanghai, but you certainly won’t want to miss any of the action when the tournament begins on Wednesday, October 1.