He was 23 when he finally ended that drought. A later slump saw him go eight Slams without a title before he ended that wait by winning Wimbledon in 2018.

From his 13th major, however, Djokovic needed only six years to reach 24. That makes his current drought historically significant.

For the first time since the early years of his career, Djokovic is facing the possibility of going three full years without winning a Grand Slam. The difference now, of course, is age.

He was 23 when he ended his first major drought. He is 39 now.

Alcaraz and Sinner have changed everythingAge is only part of the explanation for Djokovic's inability to turn deep runs into another title. The bigger factor has been the emergence of Carlos Alcaraz and Jannik Sinner.

Since Djokovic won his 24th major in New York in 2023, Alcaraz and Sinner have won 10 of the last 11 Grand Slam titles, with Alexander Zverev taking the 2026 French Open. That is perhaps the most telling statistic in Djokovic's pursuit.

He has not been pushed out of the elite. He has simply encountered a new generation that has become exceptionally difficult to beat when the stakes are highest.

Alcaraz has beaten Djokovic three times in Grand Slam finals, while Sinner has emerged as another major obstacle. Yet Djokovic's head-to-head records show why he cannot simply be written off.

He is 5-5 against Alcaraz and trails Sinner only 5-6. That is remarkable for a player approaching 40.

The difference is that the younger pair have been more effective at converting their opportunities into Grand Slam trophies. The 2026 US Open could finally give Djokovic an openingThis is what makes the 2026 US Open particularly intriguing.

The draw has presented Djokovic with circumstances that have been missing from several of his recent Grand Slam attempts. Most importantly, Sinner is absent after withdrawing with a knee injury.

Alcaraz, meanwhile, is returning after a lengthy layoff caused by a wrist injury, leaving questions over whether he can immediately reproduce his best Grand Slam tennis. Djokovic has also avoided 2026 French Open champion Zverev until a potential final.

His projected route is difficult but manageable, with a potential quarter-final against Medvedev and Alcaraz among the biggest threats in the latter stages. Compared with recent Slams, Djokovic has one major advantage: one of his two biggest young rivals is absent and the other is returning from injury.

The stars, at least on paper, appear to be aligning. Novak Djokovic (AP Photo) But Djokovic's biggest opponent may be timeThere is one factor no draw can remove: age.

Djokovic's physical resilience has been one of the defining features of his career. Even at 39, he continues to produce performances that would be extraordinary for almost any other player.

His Olympic gold medal in Paris in 2024 was proof that he could still summon his best tennis for a massive occasion. But his overall record since 2023 also reflects the realities of getting older.

He won only one title in 2024 and two in 2025, while he remains without a title in 2026 before the US Open. His last ATP Finals appearance also came in 2023, and injuries have increasingly affected his schedule.

Preparation has therefore become another question mark. Djokovic does not need to dominate the season anymore.

He needs to produce two perfect weeks. At 39, that is considerably harder.

Can Djokovic finally win No. 25?

The answer is yes — but perhaps never has a Djokovic Grand Slam campaign carried so many qualifications. He is still good enough.

The numbers prove it. Eight semi-finals or better in his last 11 Slams demonstrate that he remains capable of navigating the toughest tournaments in tennis.

Two of those runs ended in finals. But he is no longer the overwhelming favourite he once was.

Alcaraz and Sinner have won 10 of the last 11 majors. Djokovic has repeatedly been stopped at the final hurdle or just before it.

And at 39, every Grand Slam represents a diminishing opportunity to add to a record that already borders on untouchable. The 2026 US Open, however, may be different.

Sinner is absent. Alcaraz is returning from injury.

Zverev is in the other half. Djokovic has four US Open titles and 10 finals in New York, giving him a level of experience few in the field can match.

Most importantly, he still believes. Three years after his last Grand Slam triumph, Djokovic is back at the scene of his greatest recent triumph with the same target: 25.

The question is no longer whether he can reach the latter stages. He has answered that repeatedly.

The question is whether he can win the two matches that have eluded him for almost three years — and finally turn 24 into 25. At 39, it could be his last great chance.

And that could make the 2026 US Open the most compelling chapter yet in Djokovic's extraordinary pursuit of history.

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