Roger Federer reveals two worst losses of his career - and neither are Wimbledon 2019

Roger Federer has revealed the worst losses of his career, claiming both were tougher than his Wimbledon final defeat against Novak Djokovic in 2019.

The now 45-year-old was defeated by Djokovic in what would become his last ever Grand Slam final appearance. The event is remembered in tennis history for Federer prevailing in almost every statistical measure but still losing, after the Serbian staved off two match-points in the fifth.

Supporters of the Swiss superstar remain unable to comprehend how Federer was defeated, with many describing it as the toughest defeat of his career, given the circumstances.

In the event of victory, Federer would have beaten his two greatest rivals back-to-back at the staggering age of 38, with both Djokovic and Rafael Nadal still in their early 30s at the time.

The match ended 7-6, 1-6, 7-6, 4-6, 13-12 to the Serbian, yet Federer struck more aces, won more net points, break points, games overall, points overall, and hit nearly double Djokovic’s winners.

The Serbian confessed in 2025 his ‘rational mind’ still couldn’t explain what had happened, prompting Djokovic to examine the role that ‘divine connection’ and spirituality played in the match’s events.

Still, Federer disagrees with the assessment of that match as being his toughest loss ever, invoking two others from much earlier in his career.

Federer discusses Wimbledon 2008 and US Open 2009 losses

Speaking to ESPN Tennis (as per Tennis Temple) ahead of his exhibition match versus Andy Roddick at the 2026 US Open, Federer described his feelings about Wimbledon 2019, then stated his toughest defeats came at the hands of Nadal in Wimbledon 2008, and Del Potro at the 2009 US Open.

He said: “[To win Wimbledon 2019] would have been special. It would have been [beating] Rafa and Novak back-to-back at 38. I had an amazing run, played great, and I played great in the final.

“Thankfully — maybe because I’d beaten Rafa in the semi-final and I played really good in the final — I didn’t have any regrets after. I was able to move on,” claimed Federer.

“The US Open final in ‘09 against Delpo haunts me more. Because it broke an incredible streak of five [Slam wins] and I knew I was never going to get that back,” said the 45-year-old.

Federer won five consecutive US Open titles between the years of 2004 and 2008, then lost to the Argentine in a three-sets-to-two thriller in 2009. That remains the sole Grand Slam victory of Del Potro’s esteemed career, while Federer never won another US Open title post-2008.

“I felt I missed out on so many chances throughout the match,” revealed the Swiss superstar. That one is a big regret.”

Federer was up two sets-to-one in the 2009 final, and squandered opportunities to win both sets four and five versus the Argentine. The 45-year-old then added “Rafa in ‘08, as well” to the list of defeats that affected him deeply.

“That Wimbledon final versus Rafa also snapped the super streak. Funnily, I have more regrets against Rafa and Delpo than I have with the Novak match,” confessed Federer.

The Swiss maestro was simultaneously on a streak of five consecutive Wimbledon wins at the time, between the years of 2003 and 2007.

He had beaten Nadal in the final of both Wimbledon 2006 and 2007, however, the Spaniard was perceived as getting closer given the score-lines of each respective clash.

In 2006, Nadal lost three sets-to-one, then three-sets-to-two in 2007, then won in 2008’s five-set blockbuster that still remains the consensus greatest match in tennis history.

The Spaniard was up two-sets-to-zero in that match, then Federer fought back to claim sets three and four in two tiebreaks. In the latter, the Swiss superstar staved off two match-points — first with an ace, then with one of the greatest backhand passing shots in history.

When Nadal reflected on the victory years later, he described that, for the first and last time in his career, he believed he had won a Grand Slam title before the last point was over.

The Spaniard drilled a forehand into Federer’s backhand, a common tactic that Nadal often abused to secure victory against his Swiss rival, and did not anticipate a scenario in which Federer would be capable of returning the shot.

The Swiss maestro did, then proceeded to win the fourth set outright and level proceedings. Ultimately, Nadal was not to be denied, winning the match in the fifth set; a rain delay saw the showdown descend into the night-time, with the court illuminated by the lights of phones and torches.

Despite Wimbledon 2008 and US Open 2009 standing out in Federer’s mind as the two toughest losses of his career, he did acknowledge the match-points that he failed to convert at Wimbledon 2019.

“I’m the king of missing match-points, it seems like,” joked Federer. “I don’t know what happened, but it’s part of my legacy as well.”

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The interviewer quickly affirmed that it is not what the 20-time Slam champion will be remembered for; Federer will forever remain the first male player in the Open Era to reach the milestone of 20 Grand Slam titles.