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Roger Federer picks two Grand Slam misses and his greatest match — all with a US Open connection
Roger Federer returned to the US Open on Wednesday for the first time since 2019 to feature in two exhibition events during Fan Week.
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New York and the US Open finally got the chance on Wednesday to give Roger Federer the farewell he had long been denied. Seven years after his last appearance at the iconic Arthur Ashe Stadium, where he had suffered a quarter-final loss to Grigor Dimitrov in 2019, the Swiss legend returned to the scene of five of his greatest triumphs.
But there are two contrasting New York moments that remain deeply embedded in Federer’s memories, one that represents the absolute peak of his powers, and another that still carries a hint of regret.
Federer returned to the US Open for the first time since 2019 to feature in two exhibition events during Fan Week. The first was a one-set singles match against longtime rival Andy Roddick, followed by a one-set doubles contest in which Federer teamed up with John McEnroe to face Roddick and Andre Agassi.
Deep Dive
He won both matches before being given the farewell thatNew York had never really got to stage for him as a professional player. Organisers put on a spectacular drone show celebrating his five US Open titles, won consecutively between 2004 and 2008, as Federer sat alongside his fellow tennis greats.
His first triumph in New York came in 2004, against Lleyton Hewitt, a player Federer described as “one of my biggest rivals at the time”.
Until that year, Hewitt had won seven of their first nine meetings. Federer finally turned the tide in 2004, beating the Australian in the fourth round of the Australian Open, then defeating him again in the Wimbledon quarter-finals and, finally, in the US Open final.
Hewitt did not beat Federer again until the 2010 Halle final, when the Australian prevailed in three sets. Federer won their final meeting in the Brisbane final in 2014.
But it was that 2004 US Open final that Federer later identified as perhaps the best match he ever played — so good, in fact, that he was stunned by his own level.
“The best match I ever played? I feel like I have a lot — maybe when I beat [Lleyton] Hewitt in my first US Open [in 2004], 6-0, 7-6, 6-0. I just played in a dream state, and to do that in my first US Open final was like, Wow — I can reach these heights. I was shocked at my own game,” Federer told Vogue.
“Lleyton was one of my biggest rivals at the time and I used to really struggle against him, so it was an incredible match for me.”
His other favourite came from a very different chapter of his career.
Federer picked his 2009 Wimbledon final against Roddick, where he survived a brutal fifth set to win 16-14 and claim his 15th Grand Slam title.
“I think when I beat Roddick at Wimbledon — 16-14 in the fifth — in ’09. At the time, Mirka was pregnant, and it was the super summer: I had won the French Open shortly before. There was a lot riding on it,” he said.
“It’s also when I broke the all-time Grand Slam record, and Sampras, whose record of 14 Grand Slams was broken by me, was there. And it was the year after I had lost to Nadal in the final, 9-7 in the fifth. So for me to come back the year after and win it that way, with everything riding on the match, felt like a huge deal.”
Yet Federer also has two Grand Slam matches he wishes he could replay.
It would not take much guesswork to identify one: the 2008 Wimbledon final against Rafael Nadal, widely regarded as one of the greatest matches in tennis history.
The other came a year later at the US Open.
Federer’s 2009 final against Juan Martin del Potro was the match that ended his run of five consecutive US Open titles. He would never win the tournament again, reaching only one more final, in 2015, when he lost to Novak Djokovic in four sets.
“Of course you have some minor regrets where you’re like, I wish I could play that shot again, or I wish I could play that match again. Two of them are actually linked to the US Open and to Wimbledon, because they broke my streak of five in a row,” Federer said.
“Here was against [Juan Martin] del Potro in ’09, and at Wimbledon it was against Rafa — obviously the epic one in ’08.”
Federer was left to wonder what might have been had he won both.
“Winning those matches would have kept my streak [of consecutive titles] alive — I could have gone to six, or who knows, seven, because I won Wimbledon the following year again, and then again in ’09 against Roddick.”
For Federer, though, those losses have ultimately become part of the story rather than a source of lingering bitterness.
“So yeah, you have moments like these where you’re like, what a shame, because you just know in that moment when the streak snaps that you’ll never get to another five in a row — it’s just not going to happen,” he said.
“So it feels a bit disappointing and a bit bitter, but in the end, all good. It’s part of the game and I’m happy I don’t carry those losses with me today — I’ve really focused heavily on the good moments.”
And perhaps that is the most fitting way for Federer to leave New York: not with the losses that ended his streak, but with the memories of the matches that made him a five-time US Open champion.
