Despite being one of the most successful players ever, Roger Federer endured some tough losses throughout his career. These include the Wimbledon finals against Novak Djokovic in 2019 and Rafael Nadal in 2008, as well as the 2009 Australian Open final against Nadal, where he couldnât hold back tears during the trophy ceremony. So, which match would Federer most like to replay?
Before retiring, and even before his last Wimbledon, Federer answered Vogueâs famous â73 Questionsâ for the magazineâs YouTube channel. Among those questions was âWho would you like a rematch with?â His answer: âMaybe, Del Potro, US Open 2009.â
The final against Juan Martin Del Potro in 2009 was his last US Open final. The Swiss legend was going for a record of six (consecutive) US Open titles in the Open Era, breaking his tie with Pete Sampras and Jimmy Connors. However, the Argentine fought hard to win his first and only Grand Slam title in five sets.
On the other hand, ahead of Federerâs retirement in the 2022 Laver Cup, he told Eurosport that his biggest âheartbreakâ in his career was the 2008 Wimbledon final. Considered by many, the greatest match of all time, Federer lost in five sets and 4:48 hours in play time. He lost the first two sets 6â4 6â4, before recovering and winning the following two in tie-breaks 7â6(5) 7â6(8), and then, finally, lost the fifth 9â7.

Roger Federer and Juan Martin Del Potro atfer the 2009 US Open (Getty Images)
âProbably Wimbledon 2008,â the Swiss star said immediately, when asked about his biggest heartbreak. âJust because of the way it ended, in the darkness, with Rafa (Nadal). There was so much on the line it needed a winner and it went his way.â

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Nadal and Federerâs rivalry marked their careers, making each other better. In the same Voge interview in 2019, the Swiss star admitted that he dreaded playing Nadal the most, but enjoyed the matches against Nadal the most.
Meanwhile, the Spaniard, 22-time Grand Slam champion, said that their encounters felt like âchess matchesâ in a new interview with Andy Roddick. âOur matches were like a chess match; everyone knew the strategy in advance, and there were no secrets. If he played at his best, he beat me; if I played at my best, I beat him,â he said.

Roger Federer and Rafael Nadal after the 2008 Wimbledon final (Getty Images)
Nadal held a 24-16 advantage over Federer in their head-to-head matchups, dominating on clay with a 14-2 record, including several victories at the French Open. While Federer had the upper hand on hard courts (11-9) and grass (3-1).





