SIX HUNDRED AND sixty-two days have passed since Novak Djokovic last won a major title.

That day, in September 2023, was a history-clinching performance at the US Open, in which he defeated Daniil Medvedev to tie Margaret Court’s long-standing record for the most Grand Slam singles titles of all time with 24.

It seemed all but certain that Djokovic would eventually claim the outright record.

Since then, Rafael Nadal, his greatest rival, has retired from the sport, leaving Djokovic as the lone remaining member of the Big Three. (Roger Federer, the other member, retired in 2022.) The now 38-year-old Djokovic has reached a Wimbledon final, made three other major semifinals and even won Olympic gold, but the coveted record remains elusive. After losing to Jannik Sinner in the semifinals at the French Open last month, he was emotional as he walked off the court. He later told reporters it “could have been the last match ever” he would play at the tournament and hinted at his own retirement.

Even without mentioning his inevitable end in the sport, there already was a looming question mark over every major he played. But by making it clear that he knew it too, there’s almost a countdown clock on his dream and his chance to secure tennis immortality. And now at Wimbledon, an event in which he has won seven times, many of those around the game have publicly speculated that this fortnight is his best — and perhaps final — opportunity to win major title No. 25.

Now into the third round after clinically defeating Dan Evans, 6-3, 6-2, 6-0 on Thursday, and after looking mostly dominant in his first two matches, the No. 6-seeded Djokovic’s play has supported this claim. And he hasn’t hidden that he knows it too.

“Whether it could be my last dance, I’m not sure, as I’m not sure about Roland Garros or any other Slam that I play next,” Djokovic said during his news conference before the tournament got underway.

He added he wanted to keep playing, but admitted he was unsure he would be able to.

“And yes, I would probably agree that Wimbledon could be the best chance because of the results I (have) had, because of how I feel, how I play in Wimbledon, just getting that extra push mentally and motivation to, yeah, perform the best tennis at the highest level.”

For now, five matches — and potentially his two biggest rivals of the moment in Sinner and Carlos Alcaraz — stand in his way. If he were to do it, he would become the oldest player in the Open era to win a Slam, and he would match Roger Federer for the most men’s singles titles at the All England Club. Twenty years after making his debut at the tournament, so much is in his favor and the stakes are higher than ever. Can he do it?

TO BE CLEAR, Djokovic does not have to win another match to secure his spot among the sport’s greatest.

His résumé already speaks for itself. He has more major titles than any man in history and has spent an ATP record of 428 weeks ranked at No. 1, including holding the year-end distinction eight times. He has 40 Masters-1000 titles and 100 ATP trophies overall, won the ATP Finals crown seven times, has two Olympic medals, including a much-desired gold he secured last summer in Paris, and the list goes on and on. For many, Djokovic firmly cemented his status as the best ever after the victory in New York two years ago.

“There will always be watercooler debates, but it’s going to be tough, and much more difficult, for anyone to argue in any other direction outside of Novak being the greatest of all time with him at 24,” James Blake, the former world No. 4 and current analyst, told ESPN at the time.

But even if others didn’t need any more convincing, Djokovic made it clear he wanted to continue playing and winning as many titles as possible. After he finished the 2023 season with another ATP Finals title and the year-end top ranking, he told reporters he had even loftier goals for 2024.

“Well, you can win four Slams and an Olympic gold,” Djokovic said. “I have always the highest ambitions and goals. That’s not going to be different for the next year … Motivation, especially for the biggest tournaments in sport, is still present. It still inspires me to keep going.”

Of course, fate — and Sinner and Alcaraz — had other ideas. Djokovic lost to Sinner in the semifinals at the 2024 Australian Open and had to withdraw ahead of the quarterfinals at the French Open to undergo surgery for a torn medial meniscus in his right knee. He returned to Wimbledon and even made the final — his sixth in a row — but lost, for the second consecutive year, to Alcaraz. He achieved his lifelong dream of winning Olympic gold with an electric victory over Alcaraz and then was stunned in the third round of the US Open by Alexei Popyrin.

Djokovic appeared to be in near-peak form at the Australian Open in January, beating Alcaraz in four sets in the quarterfinals, and then had to retire after the opening set of his semifinal due to a hamstring injury. Throughout his struggles, Djokovic has spoken openly about his waning motivation and how difficult it’s been to continue with Nadal, Federer and Andy Murray no longer on tour.

Since Djokovic’s victory at the US Open, Sinner, 23, and Alcaraz, 22, have combined to win every major. Djokovic has had some success over the past year against Alcaraz, but he has been winless in all three meetings against Sinner since the start of 2024.

The duo has established themselves as the New Big Two, with Djokovic on the outside, looking to pull off the upset — much like he was earlier in his career against the then-more established Federer and Nadal. But Djokovic said that mattered little to him and his approach entering majors.

“In a sense you’re always hunting because you’re always going for the titles — in my also privileged position — the records and more history,” Djokovic said on Saturday. “I do feel that I’m always in that position of going for something with the attitude of trying to win rather than trying to defend … I would say it’s slightly different for me now in terms of, I don’t chase the rankings anymore in that regard, (but) I’m trying to play the best tennis in Grand Slams and trying to win Grand Slams. That hasn’t changed. It still stays the same.”

Through two matches at Wimbledon this week, and particularly in his second-round victory, Djokovic has displayed an increasingly high level of tennis. He was relentless in his overpowering of the British Evans with an 89% win percentage on first serve and 46 winners (to Evans’ 19) in the clash that lasted just 1 hour and 47 minutes.

“The bottom line is, it’s pretty obvious why he’s as good as he is on that court,” Evans said after the match. “He played good tennis and showed everybody on Centre Court why he’s a contender.”

Djokovic told the crowd after the match he executed his game plan for the match “perfectly” and said it was one of those days “where everything goes your way.” With the win, he advanced to the Round of 32 at Wimbledon for the 19th time. He will next face fellow Serbian Miomir Kecmanovic on Saturday, with a spot in the second week on the line and a chance for his 100th career victory at the All England Club. Djokovic has won all three of their previous meetings, including at Wimbledon in 2022.

GRASS HAS ALWAYS been well suited for Djokovic’s playing style and it remains the surface in which he has the biggest advantage.

Though he didn’t play on the surface as a child, or even as a junior, he has managed to adapt his movement, and masterfully utilizes his flexibility and footwork to cover the court. In addition to his strong serve and return, which are obvious benefits, he can handle the low-bouncing conditions and differing speed of the grass better than almost anyone. While some players have said the court speed at Wimbledon has slowed in recent years, Djokovic said on Thursday that grass remains the fastest surface, but added he believes the ball used has changed the pace of play somewhat. He’s seemingly adjusted no matter how fast or slow the court may be.

Grass is also the softest and absorbs impact differently than the others — something that could certainly benefit an aging player with recent leg injuries.

But perhaps most helpful to him of all, Djokovic has the experience on the surface that few others do. The grass season is undoubtedly the shortest portion of the calendar — with just over three weeks separating the end of the French Open and the start of Wimbledon — so few top players participate in more than two warmup events and some, for varying reasons, play none at all. With such a short window every year, it can be hard for players to ever truly feel comfortable on the surface, as evidenced by the rash of top-seeded players who have been upset in the first two rounds of play.

“I don’t know when the end is coming but I think his best chance is on grass,” said Andy Roddick, the 2003 US Open champion and former world No. 1, on a recent episode of his “Served” podcast. “I think his game as it stands currently — not Novak from five years ago — but as it stands currently, I think he gets the most benefit from the surface on grass now. And he knows what to do with it.”

If Djokovic were to win on Saturday, he would likely face No. 11 seed Alex de Minaur in the fourth round. While No. 4 seed and British favorite Jack Draper was Djokovic’s presumed quarterfinal opponent, Draper lost in the second round on Thursday to unseeded Marin Cilic, the 2014 US Open champion. While Cilic or Jakub Mensik, the No. 15 seed and rising teenage star, are now potential foes in the quarters, Djokovic’s draw feels more favorable in Draper’s absence. Sinner would likely await in the semifinals, and while Sinner has gotten the better of Djokovic in their recent meetings, he’s never advanced past that stage at Wimbledon before, and lost in his lone lead-in event in the round of 16.

If Djokovic were to make it to the championship match, he could set up a third-consecutive Wimbledon final against Alcaraz, the undisputed favorite to win the title. While it would be difficult to defeat Sinner and Alcaraz back-to-back on one of the sport’s grandest stages, it would not be impossible.

“He’s not at the levels of Carlos and Jannik, especially in the last 18 months, because the numbers speak for themselves, but the way he played against Sinner (at the French Open) surprised me,” former world No. 12 Feliciano López said in a recent interview with Sky Sports. “He challenged Sinner and pushed him to the limit and, although the gap is still big, I see the grass as the only place for him to get to this level that they play because the grass is very different. Djokovic proved that he can still compete at this level (and) he will have a better chance on grass.”

Djokovic is a student and fan of the game, and there’s little one can tell him about his chances or what’s at stake that he doesn’t already know. But as he basked in the adoration of the fans and the sunshine on Thursday afternoon, he admitted he doesn’t allow himself to think much about what he’s already achieved — instead saving that for a day in the future in which he can “sip margaritas on the beach with Federer and Nadal and just reflect” — but he is focused on what’s immediately in front of him.

“Wimbledon still stays the most special tournament in my heart, the one that I always dreamed of winning when I was a kid, so any history made here is obviously extra special for me,” Djokovic said. “It’s the beginning of the tournament, so yes, I’m aware of the history on the line and I’m obviously in a privileged position to do that, but at the same time, I’m thinking about the big things that I can make in this tournament.”