Alexander Zverev has straddled two generations and he’s pitted his wits against some of the best players to every play the sport.

The German arrived on the scene at the back-end of the ‘big three’ domination, and he played Rafael Nadal 11 times, Roger Federer, seven times, and Novak Djokovic 14 times.

After Federer and Nadal’s retirement, Zverev then had to deal with the emergence of Jannik Sinner and Carlos Alcaraz, who have swept the Grand Slam titles since.

Zverev has struggled against both men, losing to Alcaraz seven times in his career and tasting defeat against Sinner 11 times already on the ATP Tour.

In a recent interview, Zverev was asked who the toughest opponent of his career was and his answer was fascinating.

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Speaking to Knossi, the German said: “The toughest opponent I’ve faced is Djokovic. With Roger Federer, the record is pretty good, even though I’ve also lost several matches. He played very fast, but I was capable of playing even faster than him, which he didn’t like.

“I had a tactic against him that I executed perfectly. I beat him more often than I lost. At the start of my career, he was simply too strong physically for me.

“I was too thin and didn’t have the necessary power. Our matches were close, but I always ended up tiring. Everything changed when I was 23 or 24. From then on, I beat him three or four times in a row.”

Speaking about his rivalry with Djokovic, Zverev continued: “We’ve always played very big matches, often in important encounters. He has beaten me more often than I’ve beaten him… but he has beaten everyone more often.”

While it’s not a surprise to see Zverev opt for Djokovic as his toughest opponent, many might assume that the German would pick Sinner, such is the Italian’s dominance over the star in recent years.

Zverev has lost 11 of his 15 matches against Sinner in his career and his recent record against the world No 1 is absolutely atrocious.

Sinner’s recent victory against Zverev in the Wimbledon final was his 11th straight win against the German, which dates back to the 2023 season.

The last time Zverev managed to beat Sinner was at the US Open in that year, when the Italian was just 21 years old. Zverev toppled Sinner in five sets to confirm his place in the quarter finals of the competition.

Zverev has been knocked out of a semi final or a final against Sinner nine times in his career, so the world No 1 has had a devastating effect on the star.