Novak Djokovic is currently at a crossroads in his career.

Now aged 38, he can still produce excellent tennis and defeat anyone on the ATP Tour, but his main goal is to win more Grand Slams.

But he has one big problem at the majors and that is defeating Jannik Sinner, a man he has lost to on five successive occasions.

Sinner joined Rafael Nadal as the only players to achieve this feat against Djokovic, and the Serbian has plenty of work to do ahead of the US Open, the final Grand Slam of the season.

Novak Djokovic looks at his racket during his Gentlemen's Singles Semi-Final match against Jannik Sinner at The Championships - Wimbledon 2025Photo by Rob Newell – CameraSport via Getty ImagesChanda Rubin says Novak Djokovic has some things to address ahead of the US Open

For the second successive year, Novak Djokovic will enter the US Open without being a reigning Grand Slam champion.

The last time the former world number one claimed a major was at Flushing Meadows in 2023, and he has made just one Grand Slam final since.

Djokovic stressed his physical struggles towards the end of Wimbledon and needed to be at his best to have the best chance of beating Sinner.

But in addition to addressing his physical condition, former top 10 player Chanda Rubin thinks there are other questions Djokovic needs to answer ahead of competing at the US Open.

“I think he has exhausted every last resource and he is going to continue to do that for as long as he determines he is able,” Rubin told the Inside-In Tennis Podcast.

“I think it becomes difficult when physically you start getting these little injuries and little things which hamper you in the latter stages of a two week event, that restrict you from playing your best tennis.

“You can imagine that is what Novak Djokovic is trying feverishly to address and to get ready for the US Open, the last major of the year.

“The question is whether he is going to be able to post up for that major. Depending on how physically hampered he was and the severity of that, that can take a little while.

“I think there are some serious questions for Novak Djokovic but he is absolutely a player who is going to dot every I and cross every T and if he is or isn’t able to do it you will know he tried everything possible.”

Novak Djokovic serves at the 2025 US Open in New YorkPhoto by ANGELA WEISS/AFP via Getty ImagesNovak Djokovic is confident he will arrive at the US Open in good shape

Djokovic appeared to suffer from a muscle problem at Wimbledon.

He took a medical timeout to try and treat the issue after the second set of the semi-final against Sinner.

Now Djokovic will take some time off before preparing for the summer North American hard court swing ahead of the US Open, where he is a four-time champion.

Despite not feeling his best at present, Djokovic believes he will be ready to go by the time the action commences in New York.

“This injury will not keep me away from the tour for long, but I must admit that I have had too many problems of this type in the last year and a half,” Djokovic told Serbian media. “I am convinced that I can arrive at the US Open at the top of my shape and that I can express my best tennis.”