Novak Djokovic is once again under the spotlight as he heads into the 2025 US Open, chasing a historic 25th Grand Slam title. The Serbian legend, now 38, hasn’t clinched a major since his triumph at Flushing Meadows two years ago, and the tennis world is abuzz with speculation: can he finally break Margaret Court’s all-time record, or has the game’s new guard put a permanent roadblock in his path?
Djokovic’s quest for Grand Slam immortality has been anything but straightforward. Since his 2023 US Open victory, he’s reached the semi-finals of every major but failed to add to his tally. The rise of Jannik Sinner and Carlos Alcaraz has been the headline story of men’s tennis in 2025, with the Italian and Spaniard splitting all three Grand Slam titles between them this year. Their dominance has left Djokovic, for the first time in over a decade, looking more like a challenger than the man to beat.
It’s a narrative that hasn’t escaped the attention of former champions and analysts. Mats Wilander, the former world No. 1, believes that Djokovic’s path to a record-breaking title is steeper than ever. “Looking at the last matches that he’s played against Sinner and Alcaraz, I think he may need some help to win that 25th Grand Slam,” Wilander told Eurosport on August 23. “I think we need something to happen to them, to at least one of them, because to beat Sinner, and then to beat Alcaraz and having to beat someone like Jack Draper maybe before… that’s tough for any player, even if your name is Novak Djokovic. So I do think that he does need a little bit of help from the other guys. He doesn’t need much, but he needs a little help to take out one of the big two.”
Wilander’s view is echoed by another former star, Andrew Castle, who has been even more candid about Djokovic’s prospects. Castle, a four-time US Open champion in doubles and a respected commentator, suggested that if Djokovic does manage to secure his 25th Slam on the hard courts of New York, it might be time for him to consider hanging up his racket. “It doesn’t look like much to me,” Castle told Betway, referencing Djokovic’s chances. “I mean, it doesn’t look like to me that if Carlos Alcaraz and Jannik Sinner are around that he could win another Grand Slam.”
Castle elaborated on the perception swirling around the Serbian’s career, noting, “It looks like the perception is, he’s finished in terms of winning Grand Slams. It’s the last kind of chapter in this storied career and now we analyse what he has done. At the French Open, I believe it was his 19th quarterfinal at the French Open alone. That is what the locker room talks about. I mean, the 24 Grand Slams is obviously ridiculous. But 19 French quarter-finals... and there’s records like that everywhere and Novak’s won everything twice or three times. He’s won every single title.”
Yet, Castle also acknowledged Djokovic’s legendary resilience and the possibility of a fairytale ending. “Let’s just say he’s had a good run but how do you think that he feels about it? Well, okay, wait until Sinner gets injured and Carlos has a bad day and loses, then we can have a different conversation. But as long as those two are there, I can’t see Novak winning and it’s probably exactly what he expects people to say. If anybody can turn that round and shove it up everyone’s a****, I think he would love to do that. I think that’s absolutely magnificent, and I would love it, I would be on my feet if he could get a run going and make it 25 Grand Slams at the US, especially the place where he was disqualified that one time,” Castle added, recalling Djokovic’s infamous 2020 US Open exit.
Djokovic’s journey to this US Open has been less than conventional. After a straight-sets semi-final defeat to Sinner at Wimbledon in July, the Serbian opted to skip the summer hard court swing, focusing instead on training and family time. “I may be ‘cold’ in terms of the matches, official matches... but I have put in a lot of training in last three, four weeks. I decided not to play because I wanted to spend more time with my family,” Djokovic explained to the media. “And to be honest, I think I earned my right and have the luxury of kind of choosing, picking and choosing where I want to go and what I want to play.”
He’s made it clear that his priorities have shifted. “I’m not chasing the ranking, not collecting points, not defending anything, etc. I just don’t think about it anymore. What’s important is where I find motivation and joy. To be quite frank with you, I don’t enjoy the two-week Masters events anymore. It’s just way too long for me. My focus is mostly on the slams, and I have said that before.”
Despite not lifting a Grand Slam trophy since 2023, Djokovic did add an Olympic gold medal to his crowded trophy cabinet in 2024, proving he’s still capable of rising to the occasion. But as he enters the 2025 US Open as the seventh seed, the odds—and much of the tennis cognoscenti—are not in his favor. His first-round opponent, 19-year-old American Learner Tien, represents a new generation eager to make its mark, while Sinner and Alcaraz, both in their early twenties, have shown no signs of loosening their grip on the sport’s biggest prizes. Sinner opens against Vit Kopriva, and Alcaraz will face Reilly Opelka in their respective first matches.
Castle, reflecting on the broader picture, suggested that if Djokovic does pull off the seemingly impossible, “the moment he wins the 25th, I think he should retire. You can’t go on forever, he should play as long as he wants but personally, I don’t think he is likely to win this one or another one.”
As the 2025 US Open gets underway, all eyes are on Djokovic to see if he can defy the odds and silence the doubters one more time. Will the veteran Serbian find one last spark, or will the torch officially pass to the sport’s new kings? The action kicks off on August 25, and the tennis world waits with bated breath to see if history will be made—or if the next chapter belongs to Sinner, Alcaraz, and their peers.
