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Roger Federer picks the match from his career he wants to replay the most, ‘I should have won’

Photo by HECTOR RETAMAL/AFP via Getty Images
Photo by HECTOR RETAMAL/AFP via Getty Images
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Roger Federer enjoyed plenty of success during his career, but that’s not to say he hasn’t been left with a few regrets…

The Swiss legend won 20 Grand Slams between 2003 and 2018, carving out an almost untouchable legacy within the sport.

He did, however, lose 11 major finals, falling short against his greatest rivals, Rafael Nadal and Novak Djokovic, on several occasions.

Novak Djokovic poses with the trophy after beating Roger Federer in the 2019 Wimbledon final
Photo by DANIEL LEAL/AFP via Getty Images

Federer only lost one Grand Slam final to a player not named Djokovic or Nadal, suffering defeat at the 2009 US Open.

Reflecting 16 years later, Federer has picked that match as the one he’d most like to replay from his entire career.

Roger Federer wishes he could replay the 2009 US Open final vs Juan Martin del Potro

During an interview with Tages Anzeiger, Federer was asked which match from his career he’d like to play again.

Roger Federer looks on during the 2025 Shanghai Masters final
Photo by HECTOR RETAMAL/AFP via Getty Images

“The 2009 US Open final against Juan Martin del Potro,” he said.

“I should have won that one.

“Back then, I had back pain in the warm-up and then missed so many chances.

“That was one of the matches I shouldn’t have lost.”

Federer lost to the big-hitting Argentine in five sets, 6-4, 6-7, 6-4, 6-7, 2-6, on Arthur Ashe Stadium.

The loss was his first in New York in 2,205 days.

“It also broke my streak at the US Open,” said Federer.

Roger Federer’s US Open streak

The 44-year-old explained how he struggled with the pressure of maintaining ‘streaks’ throughout his time in tennis.

“My streak also ended at Wimbledon 2008,” said Federer.

Avoid saying the same tennis player as me quiz

“Every time a streak was on the line, the whole thing got even bigger.

“But at Wimbledon, it somehow had to be that way. Rafa had deserved it so much. That’s why I thought afterwards: That’s okay.

Roger Federer and Rafael Nadal holding their trophies after the Wimbledon final in 2008.
Photo credit should read ADRIAN DENNIS/AFP via Getty Images

“But against del Potro I should have won.”

Back in 2008, Federer lost to Nadal in the Wimbledon final, bringing his SW19 winning streak to a close.

Roger Federer’s Wimbledon streak

Despite his defeats to Nadal and Del Potro, Federer still retired as one of, if not the greatest, players of all time…

Is Roger Federer the greatest tennis player of all time?

The Swiss star won 20 Grand Slam titles, which has him third in the all-time list (Open Era).

Is Roger Federer the greatest tennis player of all time?

Only his ‘big three’ rivals, Djokovic and Nadal, managed more titles at the major tournaments.

RankNameCountryGrand Slams
1Novak DjokovicSerbia24
2Rafael NadalSpain22
3Roger FedererSwitzerland20
4Pete SamprasUSA14
5Bjorn BorgSweden11
Most men’s singles Grand Slams (Open Era)

He also spent more weeks ranked number one in the world than anyone except for Djokovic.

RankNameCountryWeeks
1Novak DjokovicSerbia428
2Roger FedererSwitzerland310
3Pete SamprasUSA286
4Ivan LendlCzechia270
5Jimmy ConnorsUSA268
Most weeks at number one

It’s tough to call Federer the greatest of all time, especially with his former rival, Djokovic, surpassing him to take a number of records for himself.

However, one thing is certain: Federer will always be remembered as one of the best to ever do it!