Roger Federer shares the two toughest losses of his career – and surprisingly, neither is Wimbledon 2019.
Roger Federer recently shared which losses felt the hardest to him, and surprisingly, they weren’t the famous 2019 Wimbledon final against Novak Djokovic.
That match was special because even though Federer played incredibly well and led in almost every stat, Djokovic managed to save two match points and won in an epic five-set battle. Fans still find it tough to understand how Federer didn’t win that day, especially since he nearly beat both Djokovic and Rafael Nadal, two of his biggest rivals, back-to-back at age 38.
The final score was 7-6, 1-6, 7-6, 4-6, 13-12 to Djokovic, but Federer had more aces, won more points at the net, and hit almost twice as many winners. Djokovic later said even he couldn’t fully explain what happened and thought perhaps some “divine connection” was involved.
However, Federer feels his hardest losses came earlier in his career. In an interview before an exhibition match in 2026, he named two matches that affected him more deeply: losing to Nadal in the 2008 Wimbledon final and to Juan Martin Del Potro in the 2009 US Open final.
Federer said winning Wimbledon in 2019 would have been amazing — beating both Rafa and Novak back-to-back at 38 — but he had no regrets afterward because he played so well. On the other hand, the 2009 US Open final sticks with him more. After winning five US Open titles in a row from 2004 to 2008, losing to Del Potro in a tight five-set match broke that streak, and Federer knew he couldn’t get it back. He missed many key chances in that match and still regrets it.
The other tough loss was to Nadal in the 2008 Wimbledon final, which ended Federer’s run of five straight Wimbledon titles from 2003 to 2007. Nadal had lost to Federer in finals before, but in 2008, he finally won in one of the greatest matches ever played. Federer remembered how he almost saved the match with an ace and a stunning shot during match points, but Nadal’s powerful forehand finally won out, even though the match had to pause for rain and finish under the lights.
Despite those two matches standing out, Federer joked about his struggles with match points at Wimbledon 2019, saying, “I’m the king of missing match points, it seems like.” But the interviewer quickly reminded everyone that Federer will always be remembered not for missed chances, but as the first man in the Open Era to win 20 Grand Slam titles—the amazing legacy he’s built in tennis.