The 24-time major champion seemed to be laughing in the face of Father Time after winning three Grand Slams in 2023 at the age of 36.
However, it is now three years since Djokovic last won a major, with Carlos Alcaraz, Jannik Sinner, and more recently Alexander Zverev, sharing the slam spoils.
Now at 39, the former world No 1's body is showing more and more signs of wear and tear, particularly at this year's US Open, where he suffered his earliest loss (first round) at a Grand Slam since 2006.
Fellow veteran Dimitrov, 35, says the game is getting increasingly more physical and even Djokovic cannot cling onto youth forever. The Serb has shown he is capable of beating Sinner, Alcaraz, and Zverev, but for how much longer is up in the air.
He told Bolavip, "The players in today's tennis are just bigger, stronger, faster, which is just a natural part of the evolution of tennis, but of course it is not easy to see Djokovic getting older, maybe struggling a bit. No matter how strong you are, it is inevitable that it will hit you eventually from a biological point of view.
"Nature calls itself and it is going to happen, and when you have been in a competitive sport for so many years, with travelling, jetlag and all that stuff, it eventually catches up with you.
"In a way I also feel like it should, you know. There are also other parts to life than tennis. We have just been put in this position, a very privileged place. I feel spoiled and we should feel that way."
While Djokovic is still 11th in the rankings, Dimitrov, who has struggled with injuries in recent years, is down in 123rd. The pair have met on 14 occasions, with Djokovic coming out on top 13 times.
Both are inching closer to hanging up their rackets for good but it remains to be seen when they will leave the sport behind.
Djokovic may still be dreaming of a 25th Grand Slam and Dimitrov his first. For now, both seem like a long shot in a young man's game.