Roger Federer Reveals His Biggest Grand Slam Regret, and It Isn’t the Djokovic Loss

Roger Federer fans were treated to an epic tribute to the Swiss Maestro at the US Open, with the 20-time Grand Slam champion playing both a singles and doubles exhibition in front of a sold-out Arthur Ashe Stadium.

Federer gave a series of interviews in the buildup to the special event, and naturally, there were questions about the Grand Slam finals he lost during his legendary career and whether any of those defeats still bothered him.

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For many who watched Federer's career unfold, the obvious answer would have been the 2019 Wimbledon final against Novak Djokovic. Federer had two match points to win the title, but failed to convert either of them as Djokovic pulled off one of the most dramatic victories of his career.

However, Federer had a different answer when asked about the defeats he regrets the most.

Roger Federer Reveals the Final He Regrets More Than Djokovic Loss

Federer admitted that winning the 2019 Wimbledon final would have been special, especially because it could have given him back-to-back Grand Slam victories over Rafael Nadal and Djokovic.

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"It would have been special because that would have been back to back Rafa and Novak. I was 38 at that time. I had an amazing run. I played great in the finals. I didn't have any regrets after the final. I was able to move on more quickly."

Instead, Federer revealed that the Grand Slam final defeat that continues to haunt him more came a decade earlier. It was the 2009 US Open final against Juan Martin del Potro.

"I think the US Open finals here in '09 against delpo haunts me more. Because it broke an incredible streak of 5 titles, and I knew I was never gonna get that back. I felt that I missed out so many chances throughout the match. And that one is a big regret I have. And maybe the Wimbledon finals against Rafa in '08 as well, which also snapped a super-streak."

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Federer's defeat to Del Potro was particularly painful because he had won the previous five US Open titles. A victory in New York would have given him a sixth consecutive championship, but the Argentine fought back from a set down to defeat Federer in five sets.

Federer also mentioned the 2008 Wimbledon final against Rafael Nadal, another defeat that ended his title-winning streak from 2003 to 2007.

Roger Federer Jokes About His Missed Match Points

Interestingly, Federer admitted that it was somewhat amusing that the Grand Slam finals he regrets most involve Nadal and Del Potro rather than Djokovic.

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The Swiss legend has had plenty of heartbreaking moments throughout his career, but he was able to look back at them with the perspective that comes with retirement.

"I'm the king of missing match points it seems like," Federer said, before adding, "It's okay. No problem."

That attitude perhaps sums up Federer perfectly. Despite the enormous success he enjoyed throughout his career, he still remembers the matches that got away, but there is no bitterness attached to them.

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After the special night at Arthur Ashe Stadium, Federer will now travel to Newport for his International Tennis Hall of Fame ceremony on August 29.

He will then return to the US Open on Monday, August 31, where he will officially receive his Hall of Fame ring during a ceremony in the night session.

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