Novak Djokovic has spent much of his career turning seemingly unreachable targets into milestones. But at 39, the Serbian great is now working against an opponent that even 24 Grand Slam titles cannot solve: time. And if his latest Wimbledon run proved anything, it is that the gap between what Djokovic can still produce and what his body can repeatedly withstand is becoming increasingly difficult to ignore.

Yet retirement does not appear to be dictating his immediate plans. Djokovic has already identified another destination on the horizon, one that would require him to remain competitive into his 40s. And someone who spent nearly five years coaching him through nine Grand Slam triumphs believes there is every reason to think he can get there.

“He says that he will play until the (Olympic) Games in Los Angeles, and we are talking about two years,” Goran Ivanisevic told Croatian newspaper Sportske novosti. “Honestly, knowing him, he is able to push it through with the schedule in which he plays, with a head that is incredible, special. It is possible. After all, he is still right behind Sinner, Alcaraz, and Zverev, or, we can do so; the four of them are above everyone else, so why not?”

Los Angeles is not merely an idea Ivanisevic has projected onto his former player. Djokovic has repeatedly made the 2028 Games part of his plans, even after finally winning Olympic gold in Paris in 2024. “Six Olympic Games is better than five Olympic Games,” Djokovic said in April. “To be sharing that Olympic experience with 10,000 other athletes, the best athletes in the world, I hope I get to experience it another time. I’m really working on it. Two years seems a very long way for me now at this stage, but I’m working on it.”

Ivanisevic’s confidence is hardly new, either. After Djokovic captured his 24th major at the 2023 US Open, his then-coach was already looking five years ahead. “No, no, he’s planning to play Olympic Games in Los Angeles,” Ivanisevic said at the time. “You know what’s going on in his head. It’s like 24 hours something to achieve.” Even after Djokovic finally captured the Olympic gold that had eluded him in Paris the following year, Ivanisevic maintained: “Considering how crazy he is, it wouldn’t surprise me to see him in Los Angeles as well.”

The results also explain why Ivanisevic has not dismissed the possibility. Djokovic has gone two years and 10 months without adding to the 24th Grand Slam title he won at the 2023 US Open, but 2026 has hardly represented a complete competitive collapse. Despite playing only five tournaments through July 21, the world No. 7 reached the Australian Open final and followed it with another semifinal run at Wimbledon.

That reduced workload is not accidental. Djokovic played 12 tournaments in 2023, 10 in 2024 and nine in 2025 before making just five appearances through this point of 2026. “The only thing that at this moment, professionally speaking, I have in my vision… is the Olympics of 2028 in Los Angeles. And playing for the national team and Grand Slams,” Djokovic said last year.

Wimbledon offered an even clearer demonstration of why writing him off remains dangerous. Djokovic’s fourth-round victory over Roman Safiullin gave him a record 106 men’s singles wins at the tournament, moving him past Roger Federer’s mark of 105. Two days later, the 39-year-old faced a far more punishing test against third seed Felix Auger-Aliassime.

What followed became the longest quarterfinal in Wimbledon history. Djokovic required five hours and 15 minutes to survive Auger-Aliassime, overcoming an ankle/calf injury scare along the way before the match eventually reached a deciding 10-point tiebreak.

Djokovic took the breaker 10-4 to complete a 7-6, 3-6, 6-3, 6-7, 7-6 victory and become the oldest Wimbledon semifinalist of the Open Era. “With a racquet and a lot of heart,” Djokovic said afterward. “These are the kinds of moments that I still play tennis for, for sure.” But the marathon also exposed the other side of the challenge Ivanisevic believes Djokovic can overcome.

Two days later, Jannik Sinner defeated him 6-4, 6-4, 6-4 in two hours and 11 minutes, and Djokovic left no ambiguity about the physical cost of his quarterfinal. “Not to take anything away from Sinner, but I didn’t physically recover after my previous 5h15m quarterfinal,” he admitted.

That distinction could become increasingly important the closer Djokovic gets to Los Angeles. After his 2025 US Open exit, he acknowledged: “It will be very difficult for me in the future to overcome the hurdle of Sinner, Alcaraz, in the best-of-five on the Grand Slams. I think I have a better chance best-of-three, but best-of-five, it’s tough.” Unlike the Grand Slams, Olympic singles matches are contested over best-of-three sets.

For now, Djokovic’s immediate schedule remains uncertain. He is on the entry list for the National Bank Open in Montreal, where main-draw play begins August 1, although his participation has yet to be guaranteed. Djokovic has not played in Montreal since 2015, but he won the Canadian event when it was held in Toronto in 2016 and last competed in Canada in 2018. With his calendar becoming increasingly selective, every decision over the next two years could matter if Los Angeles remains the destination.