In the pantheon of tennis, Roger Federer is often synonymous with grace, both in victory and defeat. Yet, even for a champion of his stature, certain losses linger longer than others, etched into memory with a painful clarity. In a revealing conversation, the 20-time Grand Slam champion recently pinpointed the one match from his legendary career that he genuinely regrets, while simultaneously noting that another, perhaps more famous, heartbreak "didn't bother him" in the same way.
The match that haunts Federer is not, as many would assume, the epic 2019 Wimbledon final where he held two championship points on his own serve against Novak Djokovic only to fall in a historic fifth-set tie-break. Instead, the Swiss Maestro looks further back, to the 2005 Australian Open semi-final, where a teenage Rafael Nadal announced his arrival on the grandest stage. "I should have never lost that match," Federer confessed, reflecting on the four-set defeat.
The Agony of Wimbledon 2019: A Sting That Faded
For many fans and pundits, the 2019 Wimbledon final represents one of the most crushing defeats of Federer’s career. The stage was set for a fairytale: Federer, at 37 years old, seeking a record-extending ninth title at the All England Club against his greatest modern rival. He was dominant for stretches, outplaying Djokovic for significant portions of the match and carving out a 8-7, 40-15 lead in the fifth set. The championship was literally on his racquet. Yet, Djokovic, displaying his now-trademark impenetrable resolve, saved both match points, one with a daring forehand return winner that clipped the line. The match eventually proceeded to a fifth-set tie-break, which Djokovic won 7-3, securing one of the most dramatic victories in the sport's history.
Surprisingly, Federer claims this monumental loss did not leave a deep scar. "The Wimbledon loss in 2019, it didn't bother me," he stated. "I played fantastic. I did everything I had to. Novak was just better in the crucial moments, as he so often is." For Federer, the quality of the match and the fact that he performed at a high level so late in his career provided a sense of closure, even in defeat. He walked off Centre Court to a standing ovation, proud of his effort, acknowledging he was simply beaten by one of the greatest big-point players the game has ever seen.
The True Regret: The 2005 Australian Open Semifinal
The match that Federer genuinely regrets is his 6-2, 7-5, 2-6, 7-6(5) loss to an 18-year-old Rafael Nadal in Melbourne. At the time, Federer was the undisputed world No. 1, having won three of the four majors the previous year. Nadal, while known as a prodigious talent, was still a raw, muscle-bound teenager playing in his first major semi-final on a hard court. Federer was expected to win comfortably. "I was just not prepared for what he brought," Federer admitted.
Looking back, Federer identifies this match as a pivotal moment that set the tone for one of sport's greatest rivalries. He believes his inability to solve the Nadal puzzle that day gave his young rival a crucial psychological boost. "I think that match gave him so much belief that he could beat me anywhere, on any surface," he reflected.
The key factors that contributed to this being his career regret include:
- The Element of Surprise: Federer was not yet accustomed to Nadal's extreme topspin, relentless intensity, and left-handed angles.
- Missed Opportunity: He felt he had the game to win but failed to execute his strategy effectively.
- The Rivalry's Foundation: It was the launchpad for Nadal's confidence against him.
A Glimpse into a Champion's Psychology
This distinction between the two losses offers a fascinating insight into the mindset of an all-time great. For Federer, the pain of a loss is not necessarily defined by the stakes or the proximity to victory, but by his own performance and the long-term ramifications. The 2019 Wimbledon final was a clean, well-fought duel where he felt he left everything on the court. The 2005 Australian Open, however, was a match where he felt he underperformed and, in doing so, inadvertently empowered a rival who would go on to challenge him for the next 15 years. "That one, I feel I let slip away," he said.
The Djokovic Dynamic: Respect Without Regret
Federer's comments also shed light on his unique relationship with Djokovic. While their rivalry was intensely competitive, Federer's perspective suggests a different kind of respect. He acknowledges Djokovic's supreme ability in pressure moments as a force of nature, almost separate from his own actions. Where the Nadal loss felt like a personal tactical failure, the Djokovic loss felt like being overcome by an inevitable tide. "With Novak, you sometimes just have to tip your hat," Federer noted.
This is not to say the 2019 defeat was easy. In his recent documentary, Federer: Twelve Final Days, footage shows him watching the match points and wincing, a clear sign of the raw emotion it once carried. But time has healed that specific wound, transforming it from an agony into a testament to his longevity and his role in a legendary contest. The sting was replaced by a broader appreciation for the narrative.
The Legacy of a Rivalry Forged in Defeat
The 2005 Australian Open semi-final ultimately became the foundation of the Federer-Nadal rivalry, a clash of styles and personalities that defined an era. Nadal would go on to win that tournament, his first major on a hard court, and just a few months later, he would defeat Federer on the Parisian clay to begin his historic reign at the French Open. That initial loss in Melbourne, therefore, was not an isolated event; it was a catalyst. Federer's regret stems from knowing that a different outcome might have altered the early dynamics of their storied competition.
In the end, Roger Federer's candid reflection provides a poignant coda to his career. It reveals that for champions, the ledger of wins and losses is measured not just in trophies, but in moments of perceived personal failure and their lasting consequences. The 2019 Wimbledon final, for all its dramatic heartbreak, is a proud memory of a battle well fought. The 2005 Australian Open, however, remains the one that got away—the single match he would most like to have back, not for the title it cost him, but for the rival it helped to create. "That's the one," he affirmed, "that I truly regret."