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Jim Courier delivers his verdict on whether this is Novak Djokovic’s last chance to win a Grand Slam before he retires

Image of Novak Djokovic reacting during his second-round win at Wimbledon in 2025, inset of Jim Courier looking on during the 2016 Davis Cup
Credit: Getty Images/Rob Newell - CameraSport/Robert Prezioso
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Novak Djokovic holds the Grand Slam record but would surely love to add another to his collection before he hangs up his racket for good.

When Djokovic beat Daniil Medvedev in the 2023 US Open final, he picked up his 24th Grand Slam title, an Open Era record.

He has, however, failed to win the elusive 25th major, coming up short in his previous six tournaments.

Novak Djokovic of Serbia looks on during the Men's Singles Semi Final match on Day Thirteen of the 2025 French Open at Roland Garros.
Photo by Franco Arland/Getty Images

Winning his opening two matches with ease at Wimbledon in 2025, Djokovic looks in great shape to contend for the title at SW19.

Following Djokovic’s second-round win over Dan Evans, one tennis legend was asked whether it’s now or never for the Serb to win another Grand Slam.

Jim Courier says Wimbledon is Novak Djokovic’s ‘best chance’ to win a Slam, not his last

During the latest episode of the ‘Tennis Channel Live Podcast’, former world number one Jim Courier was asked whether this is Djokovic’s last chance to win a major.

“I would strike the word last from there. I would say this is his best chance because he is not getting any younger and Wimbledon is a surface he is more adept at than anybody else comparatively,” he said.

“He is so at home on this surface, [Jannik] Sinner is trying to get there, [Carlos] Alcaraz is already, but he is on the other side of the draw.”

The world’s top two players, Jannik Sinner and Carlos Alcaraz, have shared the previous six Grand Slams between themselves, as they continue to dominate on the ATP Tour.

Djokovic has played the pair four times in total at the All England Club, enjoying success against one and misery against the other.

MatchWinnerLoserScore
2024 Wimbledon – FCarlos AlcarazNovak Djokovic6-2, 6-2, 7-6
2023 Wimbledon – FCarlos AlcarazNovak Djokovic1-6, 7-6, 6-1, 3-6, 6-4
2023 Wimbledon – SFNovak DjokovicJannik Sinner6-3, 6-4, 7-6
2022 Wimbledon – QFNovak DjokovicJannik Sinner5-7, 2-6, 6-3, 6-2, 6-2
Novak Djokovic’s Wimbledon head-to-head record against Jannik Sinner and Carlos Alcaraz

Beating Sinner twice, in 2022 and 2023, Djokovic got the better of the Italian, but struggled against Alcaraz, losing to him in the previous two finals.

Courier proceeded to explain why Djokovic has a better chance of Grand Slam success at Wimbledon than at the two hard-court majors.

“When you get to the hard courts which will be the next two majors after this. Yes, he’s incredible on those but the other players feel like they have their feet underneath them the way they can’t feel it here,” he said.

Novak Djokovic reacts during his second-round win at Wimbledon in 2025
Photo by Rob Newell – CameraSport via Getty Images

“So, yes, this is his best chance from here forward for him to win a major, but I think he might have other chances if he is healthy and wants to keep going.”

If Djokovic were to win the Wimbledon title, or any Grand Slam from here on in, he would become the oldest major champion in tennis history.

The oldest Grand Slam champions in tennis history

No player in the history of the men’s game has won an Open Era Grand Slam title aged 38 or above.

In fact, just one 37-year-old managed to win a Grand Slam, doing so 53 years ago at the Australian Open.

RankNameGrand SlamAge
1Ken Rosewall1972 Australian Open37 years, 1 month
2Roger Federer2018 Australian Open36 years, 5 months
3Ken Rosewall1971 Australian Open36 years, 4 months
4Novak Djokovic2023 US Open36 years, 3 months
5Novak Djokovic2023 French Open36 years
6Rafael Nadal2022 French Open35 years, 11 months
7Roger Federer2017 Wimbledon35 years, 10 months
8Ken Rosewall1970 US Open35 years, 10 months
9Novak Djokovic2023 Australian Open35 years, 7 months
10Rafael Nadal2022 Australian Open35 years, 7 months
Oldest Open Era Grand Slam men’s singles champions

On that occasion, it was Ken Rosewall who overcame Mal Anderson in straight sets to win his fourth Open Era Grand Slam.

Ken Rosewall celebrates with the Australian Open title in 1972
Photo by Fairfax Media via Getty Images/Fairfax Media via Getty Images via Getty Images

Only time will tell if Djokovic can take the record from Rosewall in 2025, but it will certainly be worth tuning in for.

Djokovic will resume his Wimbledon campaign on Saturday, July 4, when he takes on his countryman Miomir Kecmanovic for a place in the last 16.