The 2019 Wimbledon final between Roger Federer and Novak Djokovic wasn’t just a tennis match—it was a cultural moment. Five years later, fans still argue over the five-hour epic: Was it a masterpiece of resilience, or a painful reminder of Federer’s late-career heartbreak? The Hawkeye Podcast’s recent episode on Swiss brand On’s rise (and Federer’s 2019 investment) reignited the debate: Can you love Federer’s legacy while admitting his 2019 Wimbledon loss stings? The answer, for many, is a complicated yes.

The Match That Defined Federer’s Final Chapter

Federer entered the July 14, 2019 final as the favorite. At 37 years old, he’d just saved two championship points in his semifinal victory over Rafael Nadal—their 40th and final meeting. The Centre Court crowd buzzed with anticipation: Could Federer secure a record ninth Wimbledon title and 21st Grand Slam?

What unfolded was a match for the ages. Federer dominated early, winning the first two sets 7-6(5), 1-6 before Djokovic stormed back to claim the third 7-6(4). The fourth set saw Federer break Djokovic’s serve at 8-7, serving for the championship at 40-15—two points from victory. But Djokovic saved both match points, forcing a fifth set. In the decider, Federer’s serve faltered, and Djokovic broke at 4-4. The Serb held to win 7-6(5), 1-6, 7-6(4), 4-6, 13-12(3), clinching his fifth Wimbledon title.

“It was a great match,” Federer said on-court immediately after the loss. “It was long. It had everything.” His words, later reported by Tennishead, captured the bittersweet tone of the night. The loss wasn’t just a defeat—it was the end of an era.

Why the 2019 Final Still Hurts (And Why That’s Okay)

For Federer fans, the 2019 Wimbledon final represents a turning point. Here’s why the match still divides opinion:

• The Championship Points: Federer’s missed opportunities at 40-15 in the fourth set remain a sore spot. Many fans argue that if he’d converted either, the narrative of his late career would’ve shifted entirely.
• The Fifth-Set Tiebreak: Wimbledon introduced a final-set tiebreak in 2022, but in 2019, players battled until one led by two games. Djokovic’s 13-12(3) victory in the fifth set felt like a marathon within a marathon.
• The Rivalry’s End: Federer’s semifinal win over Nadal was their last meeting. The 2019 final became a symbolic passing of the torch—from Federer and Nadal to Djokovic and the next generation.

“You can love Federer’s career and still admit that loss was devastating,” said tennis analyst Ben Rothenberg in a 2023 retrospective on the match. “It’s okay to feel both pride and frustration.”

Federer’s 2019: More Than Just Wimbledon

While the Wimbledon final was the emotional climax of Federer’s 2019 season, it wasn’t his only highlight. The year began with a Hopman Cup victory alongside Belinda Bencic, where Federer defeated Stefanos Tsitsipas and even faced Serena Williams in a historic mixed-doubles match. He won his 100th career title in Dubai and claimed his 28th and final Masters 1000 trophy in Miami.

But the losses stood out too. Federer fell to Tsitsipas in the fourth round of the Australian Open, ending his streak of 14 consecutive Grand Slam semifinals. At the French Open, he lost to Nadal in the semifinals—a match that underscored the Spaniard’s dominance on clay. By the time he reached Wimbledon, the stakes felt higher than ever.

“2019 was the year Federer’s career began to wind down, but it was also a reminder of how much he still had to give,” said ATP Tour historian Luca Baldissera. “The Wimbledon final was the perfect encapsulation of that tension.”

The On Connection: How Federer’s 2019 Investment Changed the Game

Federer’s 2019 wasn’t just about tennis. That year, he made a high-profile investment in Swiss running brand On, reportedly acquiring a 3% stake for approximately $60 million (55 million euros). The move wasn’t just a financial play—it was a statement. Federer, known for his precision and elegance, aligned himself with a brand that embodied performance and innovation.

“On was already growing, but Federer’s involvement gave it global credibility,” said sports marketing expert Tim Crow. “It was a masterclass in athlete branding—tying his legacy to a company that shared his values.”

For fans, the investment added another layer to Federer’s 2019 narrative. Even as his on-court career faced uncertainty, his off-court ventures signaled a new chapter. The Wimbledon final, then, wasn’t just a loss—it was a bridge to what came next.

Why the Debate Still Matters

The Hawkeye Podcast’s discussion about Federer’s 2019 Wimbledon loss taps into a broader question: Can sports fans hold two emotions at once? The answer is yes—and it’s what makes Federer’s legacy so enduring.

For some, the 2019 final is a testament to Djokovic’s resilience. For others, it’s a painful “what if?” moment. But for most, it’s both. Federer’s career was defined by moments that transcended wins and losses—his grace under pressure, his rivalry with Nadal, his ability to reinvent himself. The 2019 Wimbledon final was the last time the world saw him as a contender for a Grand Slam title, and that’s why it still resonates.

“You don’t have to choose between loving Federer and admitting that loss hurt,” said Rothenberg. “That’s the beauty of sports—it’s okay to feel conflicted.”

Key Takeaways

• The Match: Djokovic defeated Federer 7-6(5), 1-6, 7-6(4), 4-6, 13-12(3) in the 2019 Wimbledon final, saving two championship points in the fourth set.
• The Stakes: Federer’s loss marked the end of his Grand Slam final appearances and his last meeting with Nadal.
• The Legacy: The match is remembered as one of the greatest in tennis history, but also as a turning point in Federer’s career.
• The Investment: Federer’s 2019 stake in On (reportedly $60 million for 3%) signaled his transition into business and branding.
• The Debate: Fans still argue over the match’s significance—was it a triumph for Djokovic or a heartbreak for Federer? The answer is both.

What’s Next for Federer’s Legacy?

Five years after the 2019 Wimbledon final, Federer’s influence extends far beyond Centre Court. His investment in On has helped the brand grow into a global powerhouse, with a market valuation exceeding $10 billion. On’s success is a testament to Federer’s eye for opportunity—and his ability to stay relevant long after his playing days.

For tennis fans, the 2019 final remains a touchstone. It’s a reminder that sports aren’t just about wins and losses—they’re about moments that define careers, spark debates, and exit lasting impressions. And for Federer, it was the match that proved even in defeat, he could captivate the world.

As the Hawkeye Podcast put it: You can love Federer and still hate that he lost. And that’s okay.