"For me, the most difficult match was the 1st time against Rafael Nadal in Roland Garros and the 1st time with Novak Djokovic"

Jannik Sinner recently discussed the most challenging matches he has played so far, specifically mentioning his first encounter with tennis greats Rafael Nadal and Novak Djokovic as his toughest.

Sinner is currently competing at the 2024 Rotterdam Open - his first tournament since lifting the Australian Open trophy. On Saturday, February 18, the Italian defeated Tallon Griekspoor in the semifinal, winning 6-2, 6-4, setting up a final against 25-year-old Alex de Minaur.

After Sinner's match against Griekspoor, a video was posted on X (formerly Twitter) by the official account of the Rotterdam Open in which the Italian was interviewed by a 12-year-old fan. Among other questions, the fan asked Sinner about his most difficult matches. The Italian responded:

“I've had some really difficult ones. I think anytime you play against a new player it's really difficult because sometimes you don't know what to expect.”

Sinner added that one of his most difficult matches was his first encounter with Rafael Nadal. The 22-time Grand Slam winner defeated the Italian 7-6(4), 6-4, 6-1 in the quarterfinal of the French Open in 2020.

Sinner also mentioned that his first match against Novak Djokovic in the second round of the 2021 Monte Carlo Masters was another difficult encounter. The match ended 6-4, 6-2 in favor of the Serb.

“For me personally, the most difficult was the first time Rafa in Paris and Roland Garros and the first time with Novak was very difficult I think it was in Monte Carlo. So I've had some and you always have to try to learn from that,” Jannik Sinner said.

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How Jannik Sinner has fared against Rafael Nadal and Novak Djokovic

Since turning pro in 2018, Jannik Sinner has faced both Rafael Nadal and Novak Djokovic on the ATP tour a few times.

Sinner has faced Nadal three times, and the Spaniard has been victorious over Sinner in all their matches. Their first meeting was at the quarterfinal of the French Open in 2020. They next met during the second round of the 2021 Italian Open and their last encounter was in the Round of 16 of the 2021 French Open.

Sinner and Djokovic have faced each other seven times on the ATP tour, with Djokovic winning four times. Their seven meetings include one final and three semifinals, with their most recent encounter being the semifinal of the 2024 Australian Open, where Sinner defeated Djokovic.