Novak Djokovic is still refusing to let go of his last great pursuit, but the evidence is starting to build that time is tightening around him.

His straight-sets loss to Jannik Sinner at Wimbledon earlier this month carried a different feel from the usual post-match exchanges. Djokovic later acknowledged that the five hours and 15 minutes he had spent overcoming Felix Auger-Aliassime in the previous Tuesday’s quarter-final had left too much of a toll on his 39-year-old body to cope with Sinner. That explanation was understandable, but it also underlined a familiar pattern.

What Djokovic has done by competing at this level so far beyond the point when he could have walked away remains extraordinary. Even so, the closing stages of Grand Slams have increasingly become the place where the same story repeats itself. Since the start of 2024, beating Sinner and Carlos Alcaraz has been beyond the rest of the men’s game, and Djokovic, one of the few to have done it on the biggest stages, is seeing the path to a 25th Grand Slam title widen further away with each major.

He will go to New York next month with another chance to extend his record, but if a third straight year passes without the major he most wants, questions will grow over whether he still has the drive to continue into 2027. Alcaraz’s fitness issues also leave uncertainty over his participation, and even if the defending champion plays, he is unlikely to be fully sharp after a wrist injury that has kept him out since mid-April.

Alexander Zverev and Felix Auger-Aliassime may also present serious problems on a fast hard court, while Joao Fonseca’s victory over Djokovic at the French Open in May has already altered that matchup’s balance. For now, Djokovic can still place himself among the top tier behind Sinner and Alcaraz, with Zverev part of that group. But if losses begin to come against players outside it, the possibility that his final great dream is slipping away will become harder to ignore.

Djokovic’s public tone remains upbeat, yet his latest remarks suggested a champion who knows the challenge is becoming more severe. “I want to kick their a** every day of the week,” said Djokovic, as he was asked about the two dominant players in the men’s game.

“To be honest, when I see them play, there are contrasting styles with [Roger] Federer and [Rafael] Nadal, really contrasting styles. I showed up as well, different. Three of us, we were all different.

“And now with Alcaraz and Sinner being the dominant force in tennis, these two guys remind me of myself so much. I’m like: ‘I’m playing myself from 10/15 years ago’, and it kind of hurts me to feel that on the court. I mean, I know how to crack the code, but can I?”

He also reflected on Andre Agassi’s view that retirement can arrive suddenly. “Andre Agassi is one of the all-time greats, of course. He was part of my documentary, and he said: ‘I don’t know when the end is coming for Novak, but I’m sure as hell that, when it comes, it comes fast.’

“I think he’s right. Of course, I would lie if [I said] I don’t have those thoughts. I do have them. And I don’t know if there’s a perfect way (to bow out).

“I’m still just trying to enjoy myself competing. I’m there, and we’ll have this conversation later.”

Many have wondered whether that conversation has already begun, but Djokovic keeps returning for more, even as the emotional cost of each Grand Slam mounts.

Carlos Alcaraz is preparing to move his recovery forward after the wrist injury that has kept him out since April, and Greg Rusedski believes a clear timetable is now coming into view for the Spaniard.

Alcaraz has already missed the French Open and Wimbledon after suffering the problem at the Barcelona Open. A recent social media post suggested he is still some way from full-speed tennis, with the 23-year-old seen striking the ball softly in what appeared to be an early stage of his return.

More uncertainty followed when Alcaraz appeared at the World Cup final in New Jersey, where a wrist support remained visible as he watched Spain beat Argentina.

Rusedski has now offered his view on whether Alcaraz can be ready for the US Open next month. In his assessment, the ATP Masters 1000 event in Cincinnati looks like the crucial test before the final Grand Slam of the year.

“To have any chance to play at the US Open, he’s gotta play Cincinnati,” he declared on the edition of his Off Court with Greg Rusedski podcast that will be released on Monday.

He added: “If he plays Cincinnati and the wrist holds up, that is exciting news for our sport, because we definitely need him back.

“If he doesn’t play Cincinnati, we know the US Open isn’t gonna happen and he’s been away from the game for very, very long time.

“He’s got to be smart with it because the fact he’s got to get his volume up to a certain level and you don’t want to rush it back too much.

“The 12-day event in Cincinnati might actually help him because the fact that he can have a few more breaks in between matches, but this is still a huge question marks.

“It’s not like you’re playing a two-out-of-three major. So for the women’s, it’s a little bit easier because when you go into the majors, it’s like a regular week with a guaranteed day off every week is two out of three sets. To make the jump up to three out of five sets is tough for the men.

“From what I saw from that original video, I wasn’t thinking would play at the US Open, but we need him back in our sport and we’ll find out. Cincinnati, fingers crossed he’s back because we miss Carlos. I really hope he’s back in Cincinnati and healthy.”

Rusedski also felt the wrist support made sense when Alcaraz took part in the World Cup final role. He noted that bringing the trophy onto the pitch before kick-off would have meant repeated handshakes and a risk to the injury.

“You gotta shake people’s hands a lot when you take on a tole like that at the World Cup,” he added. “If you have one person all of a sudden give you a big handshake, you’re gonna put that injury back in there. So I think it was clever that he had the tape on the World Cup.”

Venus Williams and Alexandra Eala were expected to reunite in doubles at the Washington Open, but the partnership was changed only days before the tournament began.

The two had already shown they could work well together earlier in the year at Bad Homburg. On that occasion, they advanced to the quarter finals before losing to Tereza Mihalíková and Olivia Nicholls, a run that suggested the pairing had real potential.

Their entry for Washington was initially confirmed, but the plans were later revised. Williams will now partner Diana Shnaider, while Eala will not take part in the event. Williams addressed the switch at her pre-tournament press conference and made clear that the timing was frustrating, even if the door is not closed on a future reunion.

Speaking at her pre-tournament press conference, Williams said: “We had a great time playing at Bad Homburg so we were looking forward to playing again.

“[It] didn’t work out this time,” the multi-time Grand Slam champion added. “Would love for there to be future times. We’ll see what happens.”

Both players have spent much of the year exploring different doubles combinations with other WTA Tour names. Eala has teamed with Janice Tjen, Iva Jovic, and Nikola Bartunkova, while Williams has played alongside Elina Svitolina, Katie Boulter, and Leylah Fernandez.

The two will still be in the singles draw in Washington, and both face difficult opening assignments. Eala opens against Olympic Gold Medalist and former Grand Slam finalist Qinwen Zheng, who is in the main draw on a wildcard. Zheng has dealt with several injuries over the past year and sits outside the top 100, but she is still viewed as a far more testing opponent than her ranking suggests.

Williams is scheduled to face Anastasia Potapova, another wildcard entrant. Potapova has produced strong results this season, especially during the European clay court swing, reaching the final in Linz, the semi finals in Madrid, and the round of 16 at both the Italian Open and Roland Garros.

Hard courts may present a different challenge, but Potapova will still be a stern first-round test for Williams, who has not won a singles match this year. Her last singles victory came exactly a year ago at the 2025 Washington Open, when she beat Peyton Stearns before falling to Magdalena Frech in the next round.