Novak Djokovic is widely considered one of the greatest tennis players of all time, with many fans of the sport adamant he is number one.
Djokovic clinched his 100th career title at the Geneva Open and is in pursuit of a record-breaking 25th Grand Slam at Roland Garros.
The Serb has won it all in tennis, putting the final piece to the puzzle when emerging victorious at the Paris Olympics, where Djokovic beat Alcaraz to earn a maiden gold medal.
Despite his dominance in tennis for nearly two decades, the former world number one has had his fair share of defeats.
Recently, Djokovic spoke on the loss that hurt him the most, which didn’t come at a major.

Novak Djokovic picks the defeat that hurt him the most in his career
Djokovic recalled his appearance at the Rio Olympics in 2016 on the Neuspjeh prvaka Youtube channel.
He said: “I had for a year and a half the best results of my life. At that point, I had all four Grand Slam titles in a row. It doesn’t get better than that.
“I came to Rio four days early. The conditions I trained in were perfect, ideal for me. The bounce, the balls, the speed, the air, everything was perfect.
“I was training fantastically. Playing those practice matches, I was crushing everyone left, right and centre. Then comes the day before the match.
“I’m playing singles, and I’m also preparing for doubles because I was playing with Zimonjic in doubles. I played that singles match for two hours, and I think I’ll do two more for doubles. I played that too. I finished, and then my wrist started to hurt.
“I think it’s just a little fatigue. The physio takes a look at it. But the next morning, I woke up and I could not move. One day before the match. What do I do? Shock! I get injections and every possible pill to go out and play, but it wasn’t right. I could not hit my backhand.
“I played an okay match, and I don’t want to take anything away from Del Potro, who beat me in the first round. I had a very tough draw, and he ended up winning the silver for Argentina. But for me, that might be the most painful loss. Given the moment I was in and how everything was unfolding.”

Novak Djokovic says why he struggled to get past the semi-finals at the Olympics
Speaking on his record at the Olympic games, Djokovic continued: “I have always played well at the Olympics, but I just could not get past the semi-finals, and it’s really interesting how that all played out.
“In 2012 I played against Andy Murray at Wimbledon. I lost a very tight match in two sets, but I had so many chances. If I could go back, I’d replay those matches.
“And again I lost to Del Potro on another court, same thing, interruptions, rain and so on. But I already won bronze [before], and I was fighting for it again.
“I wanted to win, but I was emotionally drained from the loss the day before, and it was really hard to get going.
“I experienced that twice – in London and in Tokyo. In Rio, I was probably at the absolute peak of my career.”
Prior to Djokovic’s triumph in 2024, he had only won one medal at the Olympics: a bronze in singles at the 2008 Games in Beijing.
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