“Ever since I won my 99th, which was the Olympic Games in Paris, I’ve been playing with the prospect of winning the special hundred titles.” That was the honest admission of 24-time slam king Novak Djokovic earlier this season while he was longing for the 100th ATP career trophy. And when he did achieve it, it turned out to be a special occasion for him. After capturing Geneva, he had to confess “how difficult it is to sustain this level of craziness from me on the court,” considering he is now 38. Currently, he is still going on and striving toward that magical 25th slam. But despite clinching nearly every milestone so far, there is one rare feat he may never accomplish.

Yes, Djokovic has been No. 1 for the most number of weeks (428). Yes, he has reached the most Grand Slam semifinals (53), apart from being the oldest (at 38 years, 94 days) to do so at this season’s US Open. But Djokovic is still a human who can’t achieve every record. One such milestone is the most ATP titles. Currently, the feat belongs to ex-American icon Jimmy Connors. The latter won 109 ATP titles in his career, which is still an untouched figure. 20-time slam winner Roger Federer did come close to it, winning 103 ATP trophies. But then he ended up retiring in 2022, leaving himself second on the list.

Djokovic became the third player ever, this year, to complete 100 ATP titles. However, according to top coach and 23-time slam queen Serena Williams’ former trainer Patrick Mouratoglou, the Serbian may not reach Connors’ record at all. Per Mouratoglou, Federer and Djokovic are the only two players who are close to beating the milestone. Unfortunately, the Swiss Maestro can’t do it, as he is no longer active. Speaking of the Serbian, he underlined, “I don’t think that Novak will beat it because he is focused only on the Grand Slams, which would mean, to win 6 or 7 more Grand Slams. I don’t think it is going to happen.”

Mouratoglou thinks Connors’ record “will not be beaten soon, but I think one day it will be beaten. It’s a lot. It’s a very, very high record. But I think some players in the future will win more than 109 titles in their career.”

One can also assume that Djokovic may not be able to even come close to Connors’ feat. It is because he is way past his prime form of winning back-to-back titles. Nowadays, he surely manages to make deep runs in slams. But lifting a title is not common for him anymore thanks to growing competition from the likes of Carlos Alcaraz and Jannik Sinner. Not to mention his own physical limitations.

Novak Djokovic’s tennis journey gets gloomy owing to fitness woes

This month has been extremely harsh for Novak Djokovic in terms of suffering on the court. Perhaps the growing age is reflecting on his performances every week. It became evident when he was seen fighting through the harsh weather conditions in Shanghai.

The increasing heat and humidity were such that the Serbian was seen vomiting during matches. “It’s brutal when you have over 80 percent humidity day after day, particularly for the guys when they’re playing during the day with heat; with sun, it’s even more brutal.”

On a different instance, he had to take a medical timeout regarding an issue in his right ankle. Then during the Six Kings Slam exhibition event last week, he was forced to retire. The former World No.1 was playing the match for third place against America’s Taylor Fritz. Due to a problem in his left leg, he decided to walk off the court.

“I want to apologize to everybody, sorry guys, I’m sorry you couldn’t see the second set,” Djokovic expressed frustration and apologized to the crowd in Riyadh after retiring mid-match.

Later, however, he did mention that he will look to come back next season. “Thank you all for treating me so well, I hope to return next year. Now I have to rest and address some issues I’m having with my body. I hope I can play the last tournaments of the season.” Moving forward, it will be intriguing to see whether Djokovic can take care of his fitness woes before entering the 2026 season.