Novak Djokovic is still searching for an elusive prize.
He already holds the record for the most Grand Slam men’s singles titles in history. Djokovic is the only male player in history to win each Grand Slam at least three times and has a winning record over both of his greatest rivals: Roger Federer and Rafael Nadal.
However, for all of Djokovic’s achievements, he still thirsts for more.
The 38-year-old is looking to separate himself from Margaret Court, as both players hold the record for the most Grand Slam singles titles.
Tim Henman, a former Wimbledon semi-finalist, spoke to Tennis365 after Djokovic’s Olympic victory last year. The Brit made a particular prediction about the Serbian star, which is yet to come true.

Tim Henman predicted Novak Djokovic would win more major titles
Former British number one Tim Henman weighed in on Djokovic’s chances of winning another Grand Slam.
The Serbian star had just won an elusive gold medal at the Olympic Games, defeating Carlos Alcaraz in the final 7-6 7-6 on the Paris clay.
However, he has failed to win a Grand Slam since the 2023 US Open; a two-year drought for the 38-year-old.
Speaking exclusively to Tennis365 at a Vodafone Play Your Way To Wimbledon event in 2024, Henman said: “I just don’t think the way he works means he will think he has won the gold medal and that’s it.

“He still has an enormous passion for the game. He loves what he does and if anything, it might go the other way.
“Winning the Olympics might free him up. He might think he has ticked all the boxes and I am playing with the house’s money now. He might go out and feel no pressure as he looks to win another major at the US Open.
“That might be dangerous for the rest because he will play with freedom and while he is fit and healthy, I definitely think he has more major titles in him.”
Can Novak Djokovic break his own record?
You can never write off Novak Djokovic.
The 24-time major champion has failed to win a Grand Slam for two years. However, he picked up his 100th ATP Tour title in Geneva earlier this season and has reached the semi-final stage at each of the Grand Slam events in 2025.
At 36 years old, Djokovic became the oldest winner of the US Open Men’s Singles title in Open Era history.
The 38-year-old has been prolific on hard courts throughout his career having won 14 of his 24 majors on the surface.
Included in those titles are four US Opens. He has also reached a further six US Open finals during his career.
The looming presence of Jannik Sinner and Carlos Alcaraz will be a concern for the Serbian player. Djokovic has certainly struggled against Sinner in recent times, losing to him in the French Open and Wimbledon semi-finals.
However, Djokovic defeated Alcaraz in the Australian Open quarter-finals, proving he still has the capacity to defeat the very best on the ATP Tour.
The 38-year-old withdrew from this week’s Canadian Open, which could give him ample rest to prepare properly for the Cincinnati Open and US Open.