Novak Djokovic feels like part of him left tennis when Roger Federer and Rafael Nadal retired from the sport, according to Grigor Dimitrov. The Bulgarian former world no. 3 has revealed that he has discussed the feeling with the Serbian superstar.

Djokovic, Federer and Nadal have each won 20 or more Grand Slams, and dominated the tennis scene for almost two decades as a trio. But while Djokovic soldiers on aged 39, in search of his 25th slam, Federer retired in 2022 and Nadal 2024.

Dimitrov believes the trio form the three best players of all time and claimed just one win in 14 outings versus Djokovic, one in eight against Federer and one in 15 against Nadal. Nevertheless, he heralds their era as an impossible time to recreate.

Despite now falling to the 127th best-ranked tennis player in the world, he suggested that facing those icons was the greatest challenge in the sport. He, like Djokovic, feels at a loss now that two of them have departed the game.

“A part of me left tennis when Federer and Nadal retired. I know Novak feels the same way because I talked to him about it,” Dimitrov told Danish outlet SpilXperten.

We reminded ourselves how exciting that era was, with all those challenges we had to overcome constantly.

“Having to face the three best players of all time almost every week was an incredible feeling. Today, it’s impossible for me to experience something similar.

“I don’t want to offend any player today but the big three era will always remain, for me, the greatest challenge a tennis player could face.”

Dimitrov, 35, has even conceded that he has lost a degree of passion for the sport. “I have to be honest. For a few years now, I have been very far removed from everything that happens on the ATP tour,” he said.

“I continue to play but I no longer care as much about everything that goes on in my sport and I am no longer really informed.

My whole life has always revolved around tennis and it makes me a little sad to see that I don’t even know the majority of players who are still active.”

He added: “Age may just be a number but, in our sport, it has a great influence. It’s not just about what happens on the court but also the interactions with others at tournaments.”

Dimitrov failed to qualify for a Grand Slam for the first time in 16 years when he missed out on the draw for French Open. He was given a wildcard for Wimbledon and claimed wins over Jakub Mensik and Matteo Berrettini before losing to Arthur Fery in a five-set clash.

He also attended the US Open but was defeated in four sets in the opening round against Alexei Popyrin, despite having taken the lead in the match.

Dimitrov most recently competed in the Davis Cup, where he beat Elmer Moller and lost to Holger Rune as Denmark progressed at the expense of Bulgaria.