“Wimbledon… it was, is, and still remains and always will be the most special,” Novak Djokovic said after making it to his record 52nd Grand Slam semifinal. Yes, you read that right. Then again, the Serbian legend is looking to make history as he searches for his 25th Grand Slam title.

The road to that coveted, historic 25th Grand Slam title will go through an ambitious Italian. Jannik Sinner, the world No. 1 with a 15-year age advantage, will look to end Nole’s run to a historic win at Wimbledon in the semis. However, there’s a lot more at stake for the Serbian tennis legend than just winning his 25th Grand Slam. A win this year will give Djokovic a seat beside the undisputed king of the grass court.

How many Wimbledon titles has Novak Djokovic won, and in which years?

You see, Djokovic wasn’t exaggerating when he said the oldest Grand Slam tournament in existence was the ‘most’ special to him. Of the tennis icon’s 24 Grand Slam titles, seven have come from victories at the All England Club. The 10-time Australian Open winner won his first Wimbledon title in 2011, then consecutively in 2014 and 2015, before going on a four-year win streak from 2018 to 2022.

Yet, the seven-time winner is not quite there in the Wimbledon record books. That title still belongs to perhaps Novak Djokovic’s greatest grass-court rival, Roger Federer. With eight Wimbledon titles to his name, the Swiss legend remains the king of the grass court, at least for now. However, Djokovic, who holds the record for reaching the most Grand Slam finals with 37 appearances, has come close to beating Federer’s record, reaching the finals nine times.

How do Djokovic and Federer compare in Wimbledon wins, stats, and records?

While Roger Federer still holds the Wimbledon record with eight titles, the four-time US Open winner is knocking on the door. Looking back at Federer’s Wimbledon run, the 20-time Grand Slam winner won the grass court title a record-setting five consecutive times from 2003 to 2007. That’s one more than Novak Djokovic. His other three Wimbledon titles came in 2009, 2012, and 2017.

Although winning this year will tie Djokovic with Roger Federer, the 38-year-old can’t realistically beat the Swiss icon’s five-time consecutive win record. While the Serbian was on track to equal that record, too, his 2023 final loss to Carlos Alcaraz derailed that train. Then again, Djoker has the upper hand when it comes to their head-to-head Wimbledon clashes.

Novak Djokovic and Roger Federer met on the grass court four times, including three finals and one semifinal. While Federer beat the Serbian star in their 2012 semifinal clash, Djokovic won the three Wimbledon finals in 2014, 2015, and 2019. And that begs another question.

Does Djokovic have a higher win percentage than Federer on grass at Wimbledon?

Novak Djokovic holds the lead over Roger Federer when it comes to their head-to-head battles during Wimbledon. That being said, there’s good reason why many still regard the 20-time Grand Slam winner as the greatest grass-court player of all time. After all, the Serbian is still a little behind Federer in the total number of wins at the grass-court major. While the Swiss maestro has 105 victories to his name, the 38-year-old recently crossed the 100 Wimbledon matches mark against Miomir Kecmanovic last Saturday. Since then, he has played and won two more matches, taking his tally to 102. But then again, that’s not the full story.

Rodger Federer also lost 14 of his Wimbledon matches, and thus has a win percentage of 88.23. Djokovic has a slight edge in that regard with a win percentage of 89.74, having lost only 12 matches at the oldest tennis tournament.

Now, the Serbian has the chance to widen the gap. Unfortunately, that’s easier said than done because Jannik Sinner’s No. 1 ranking and age advantage aren’t the only threats. Djokovic has an injury and is against Fabio Cobolli in the quarterfinals. It was a nasty fall. That happens on the grass,” Djokovic later said about the fall.

“I’ve had quite a few of those throughout my grass court career, but obviously, body is not the same today like it was before. I guess the impact of what happened I will feel tomorrow,” added the three-time French Open winner. Now, only time will tell if that fall has a detrimental effect on the 38-year-old’s record-setting attempt at his eighth Wimbledon title.