With a career that boasts 20 Grand Slam titles, 103 ATP singles trophies, and an astounding 310 weeks ranked as the world’s number-one player, Roger Federer’s name is synonymous with tennis excellence and longevity. For nearly two decades, he was a dominant force, captivating global audiences with his graceful, all-court style and a record-breaking streak of 23 consecutive Grand Slam semifinals. His era of supremacy included historic runs, such as winning five consecutive US Open titles from 2004 to 2008, a feat that cemented his status as one of the sport’s greatest icons.

Yet, even for a champion of his caliber, there exists one defeat that continues to stand out as a profound regret, a single match that he would choose to replay above all others. In a candid reflection on his career, the Swiss maestro has pinpointed the 2009 US Open final against Juan Martín del Potro as the one match that got away.

As reported by We Love Tennis, Federer opened up about this lingering disappointment, stating, “The 2009 US Open final against Juan Martin del Potro. I should have won that match. At the time, I had back pain during the warm-up and then I missed so many opportunities. It’s one of the matches I shouldn’t have lost. It also ended my winning streak at the US Open.”

The loss to del Potro remains uniquely painful, a solitary blemish on an otherwise spectacular chapter of his career. The context of the 2009 season makes this defeat especially poignant. That year had been a monumental one for Federer; he had finally captured the French Open to complete the career Grand Slam, reclaimed the world No. 1 ranking, and broken Pete Sampras’ record for most major singles titles by winning Wimbledon.

However, the powerful Argentine, in the midst of a spectacular tournament that also saw him defeat Rafael Nadal in the semifinals, staged an incredible comeback. Del Potro ultimately prevailed in a hard-fought five-set battle, with a final score of 3-6, 7-6(5), 4-6, 7-6(4), 6-2, to claim his first and only major title. However, recently, Federer also revealed a certain phase of his career.

Roger Federer opened up about one of his toughest moments

Roger Federer recently shared his thoughts on one of his toughest challenges in tennis, saying, “The most difficult thing for me was the transition from juniors to the pros. At first it was super cool. Suddenly I was in the locker room with Pete Sampras, Andre Agassi, Tim Henman, Yevgeny Kafelnikov, Carlos Moya and others. And I thought: This is the best! But then everything got so serious. One guy wraps the grip tape around his racket with a grim expression, and you think: Oh God, he’s intense!”

He went on, saying, “Another walks past you without giving you a glance. And you think: He wants to win at all costs! And yet: Is it really that important? That phase was tough for me. When you travel a lot, lose often, and are as emotionally charged as I was, you think: I didn’t read the fine print in the tennis contract. It’s not all fun and games. This seriousness got to me. The years from 18 to 20 or 21 were hard for me.”

Contrast this picture of the unflappable champion Federer would later become with this emotionally charged phase that he characterized as being defined by frequent travel and losses.