When Roger Federer finally called it quits after his disheartening Laver Cup 2022 men’s doubles final loss, an era came to an end. He partnered with long-time rival and friend Rafael Nadal in the match, who represented Team Europe, and was defeated by Team World’s Frances Tiafoe and Jack Sock 6-4, 6(2)-7(7), 9-11 on Saturday, September 24, in London.

The Swiss maestro has won 20 Grand Slam singles titles in his career, and is the third-highest Grand Slam singles champion in the history of the sport, behind Rafael Nadal (22) and Novak Djokovic (21). His last Grand Slam men’s singles title came in the 2018 Australian Open when he defeated Marin Cilic in the final.

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Federer has also won titles in doubles, the most notable of which came in the Olympics in 2008, when he won the gold medal, partnering with Stanislas Wawrinka. The duo also defeated Indian duo Mahesh Bhupathi and Leander Paes in the quarterfinals on their road to the final.

However, while Federer has been one of the best players in the history of tennis in singles, he was once beaten by Leander Paes, who is considered to be the best tennis player India has ever produced, at an event. To put things in perspective, Federer has won 20 Grand Slam singles titles, whereas Paes has a total of 18 doubles and mixed doubles Grand Slam titles to his name.

Paes’ victory against Federer came at the Indian Wells Masters in the United States in 2000. While Federer turned pro in 1998 and did not win his first Grand Slam title since five years later, in 2003 at Wimbledon. Meanwhile, Paes was a highly regarded doubles player back then but also tried his luck in singles. The Indian star had won an Olympic medal and another Wimbledon doubles title by the time he faced the Swiss maestro.

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Federer won the first set 5-7 against Paes at the 2000 India Wells match. The Indian scripted a comeback in the next two sets, defeating Federer 6-1, 6-4. Leander Paes later spoke about the match to the Times of India in 2020.

“I beat him at the Indian Wells qualifying in 2000. Federer was an upcoming player then. He rifled a backhand against me with a straight arm, straight up the line that went like a laser beam. My god, I had never seen anyone do that. Not even Andre Agassi,” Paes said. He went on to dub Federer the greatest tennis player of all time.