Novak Djokovic’s name has become synonymous with tennis greatness, but even in the twilight of his illustrious career, the Serbian icon continues to defy expectations and rewrite the record books. As the 38-year-old gears up for a return to the court at the Indian Wells Masters this March, the tennis world is still buzzing from his remarkable run at the 2026 Australian Open and the milestones that may yet await him this season.
Djokovic’s journey through the 2026 Australian Open was nothing short of astonishing. After not reaching a Grand Slam final since Wimbledon in 2024, many doubted whether he could truly challenge the likes of Carlos Alcaraz and Jannik Sinner at this stage of his career. In 2025, he had made the semifinals at all four Majors, but the aura of invincibility that once surrounded him seemed to have faded. Yet, as so often before, Djokovic found a way to silence the skeptics.
Opting not to play any official tournaments in the lead-up to Melbourne, Djokovic arrived at the Happy Slam in peak condition. He navigated the first week with clinical efficiency and caught a break in the later rounds, benefiting from the retirements of Jakub Mensik and Lorenzo Musetti in the round of 16 and quarterfinals, respectively. But it was his performance in the semifinals that truly stunned the tennis community. Facing world No. 2 Jannik Sinner, Djokovic prevailed in a gripping five-set battle, a match that will surely be remembered as one of the defining moments of his late career. Ultimately, he fell to Carlos Alcaraz in a hard-fought four-set final, but the message was clear: Djokovic was still a force to be reckoned with.
Chris Eubanks, speaking on Andy Roddick’s podcast, offered insight into the key to Djokovic’s longevity. “Many players who I have spoken with who have played this person say the one area of his game that doesn’t get talked about nearly enough is Novak. They say he is one of the most clutch servers ever! To see what it used to look like and what it is now is incredible.” At nearly 39, Djokovic’s serve has become a weapon that keeps him competitive against the younger generation.
As Djokovic prepares for Indian Wells—often called the ‘fifth Grand Slam’—he stands on the brink of yet another milestone. His career prize money total, as of February 27, 2026, sits at an eye-watering $192,688,360. Last year alone, he amassed $5,127,247, including $1,435,985 from his Australian Open exploits last month. With the $200 million barrier tantalizingly close, Djokovic may need to add another Grand Slam title to his collection this year to reach that landmark. Yet, in a candid November 2025 interview on Piers Morgan Uncensored, Djokovic downplayed the significance of his financial achievements. “I don’t like to talk about it, Pierce. I don’t like it. I’m north of one million (smiling),” he said, sidestepping attempts to pin down his net worth. He explained, “Money is very important and it does bring security, no doubt about it, and it is absolutely you know, one of the driving forces of the society of today. You cannot neglect the importance of money. But if money is the only thing you’re thinking about … I mean at least in my case and in my experience obviously I’m an athlete so for me it’s kind of a meritocracy model. If I win a tennis match or win a tournament I get rewarded. I get sponsorship deals etc.”
Djokovic’s wealth has been further bolstered by lucrative sponsorships with brands like ASICS, Lacoste, Hublot, Waterdrop, Aman Resorts, and Qatar Airways. Still, he insists that his brand partnerships are carefully chosen: “I have, and again I don’t like to talk about this too much, but I did refuse a lot of the big brands and big paychecks in my career because I cannot represent something that I don’t believe in. I feel like I’ve always tried to play a long game.”
While Djokovic’s modern-day dominance is clear, his legacy is also shaped by the fierce rivalries that defined an era. Gael Monfils, himself a former world No. 6, recently reflected on his battles with the ‘Big Three’—Roger Federer, Rafael Nadal, and Djokovic. Speaking on the Silver State Sports & Entertainment Network, Monfils singled out Djokovic as his toughest adversary. “Of course, for me, number one is Novak Djokovic. I never beat him. I never beat him. And so far, maybe this year is my last chance if I have to face him,” Monfils shared. “But for me, Novak has this capability to actually answer all my questions. Because tennis is a lot of questions. You ask, you answer, you ask, you answer. He was just too good. And of course, he is a legend of our sport. So no shame in that.”
The statistics back up Monfils’ claims. He finished his career with a 0-20 record against Djokovic—a stark reminder of the Serbian’s dominance. Against Nadal, Monfils managed two victories, both at the Qatar Open, while he notched four wins over Federer at various prestigious events. Monfils’ experiences echo those of countless players who spent their best years trying to solve the puzzles posed by the ‘Big Three.’
Indian Wells has long been a proving ground for tennis legends, particularly during the era of Federer, Nadal, and Djokovic. From 2004 to 2017, 13 out of 14 editions of the tournament were claimed by one of these three icons. The lone exception came in 2010, when Ivan Ljubicic produced a fairy-tale run to the title. Ljubicic snapped a five-match losing streak against Djokovic in the fourth round, then staged comebacks against Juan Monaco and Rafael Nadal before toppling Andy Roddick in two tiebreaks in the final. Reflecting on his triumph, Ljubicic said, “I mean, looking at my career, you know, in general, I did feel like, you know, I was missing it (a Masters title). It’s a really fantastic feeling to finally have it. You know, it gives something special to your career.”
As Djokovic returns to Indian Wells, memories of past glories and upsets loom large. Last year, he suffered an early exit at the hands of Botic van de Zandschulp, a result that serves as a reminder that even the greatest can falter. Yet, with his form peaking after Melbourne and the possibility of a final season on the horizon, Djokovic’s hunger for success is undiminished.
With rising stars like Carlos Alcaraz and Jannik Sinner eager to challenge his supremacy—and perhaps one day threaten his staggering prize money record—the stage is set for another captivating chapter in tennis history. For now, all eyes are on Novak Djokovic as he prepares to take on the world once more, his legacy still very much a work in progress.