We’ve argued before that the 2025 men’s tennis season has belonged to two names: Jannik Sinner and Carlos Alcaraz. Of the three Grand Slams already contested this year, Sinner has claimed two, while Alcaraz has taken one. The script was much the same in 2024, with the Italian and the Spaniard splitting four titles between them.
To find a different storyline, you have to look back to 2023 — the final chapter of the Djokovic era — when the Serbian captured three majors, surrendering only Wimbledon to Alcaraz. Since then, the so-called ‘sandwich generation’ has found little space at the table. Zverev, Medvedev, and Fritz have reached finals, but none managed to wrestle a trophy away from the Sinner–Alcaraz duopoly. It all feels reminiscent of the Big Three’s reign, when Federer, Nadal, and Djokovic rarely left openings.
Yet tennis always finds its moments of rupture. Today, we look back at five unforgettable upsets — moments when the immovable giants were toppled, when underdogs broke through and breathed fresh air into the sport.
It doesn’t get more iconic than two future Hall of Famers colliding under the lights: Pete Sampras vs. Marat Safin. The year was 2000, and across the net from Sampras — the US Open’s youngest champion at 19 and already a four-time winner in New York — stood a 20-year-old rising star from Russia.
Sampras, the defining figure of ’90s tennis, had amassed 14 majors in just 12 years, a record for his era. Enter the charismatic Safin. Born in 1980 and raised in Moscow’s southern Chertanovo district, he broke into the top 100 at just 18. Inspired by compatriot Yevgeny Kafelnikov, who delivered Russia’s first Grand Slam triumphs in 1996 (Roland Garros) and 1999 (Australian Open), Safin was determined to carve out his own legacy.
On that September afternoon, he did exactly that. In just 1 hour and 38 minutes, the fearless 20-year-old dismantled one of the game’s greatest champions, sweeping Sampras aside 6–4, 6–3, 6–3 in an unforgettable final. The victory propelled Safin to World No. 1, a spot he would hold for nine weeks, and etched his name into tennis history.
Roger Federer lifted his first US Open trophy in 2004. By 2009, he had made the tournament his personal kingdom — winning five straight editions and standing shoulder to shoulder with Pete Sampras and Jimmy Connors as the Open Era’s greatest champions in New York. But every reign has its downfall. And for Federer, the end of his US Open dominance came at the hands of a towering 1.98m Argentine with thunder in his racket: Juan Martín del Potro.
Del Potro, born in the hill city of Tandil, had already marked himself as special. He cracked the Top 10 in 2008 at just 19, riding a remarkable 23-match winning streak. By 2009, he had beaten Rafael Nadal in Miami, reached the Roland Garros semifinals and demolished Nadal again in New York (6–2, 6–2, 6–2) to set up a final against 28-year-old Federer as the World No. 6.
What followed was an epic that has entered US Open folklore. Federer, who had won all six of their previous encounters, looked set to extend his rule: he took the opening set, then watched del Potro snatch a tight second-set tiebreak. The Swiss regained control in the third, but the Argentine refused to fold. Down the stretch, Federer twice came within two points of victory, only for del Potro to drag him into a fourth-set tiebreak — and win it. In the decisive fifth, del Potro’s raw power finally overwhelmed the champion. Racing ahead 5–2, he sealed the match 6–2 on a Federer error, collapsing to the ground as Arthur Ashe erupted.
It was one of New York’s greatest upsets, the night an Argentine giant ended Federer’s reign — and the night Federer would lift his last trophy in Flushing Meadows.
Few players can claim a winning record against Novak Djokovic in ATP finals. In fact, only two men ever have: Andy Murray, often called the ‘fourth’ member of the Big Three, and Stan Wawrinka, who holds a 3–2 edge over the Serbian in title matches.
Wawrinka’s legacy is built on three Grand Slams in just three years — the 2014 Australian Open over Nadal, the 2015 Roland Garros over Djokovic and, in 2016, his greatest encore. Ranked World No. 3 heading into the US Open final, Wawrinka had already dismissed Juan Martín del Potro in the quarters and Kei Nishikori in the semis. His one-handed backhand, the envy of the tour, was in full flow. Across the net, Djokovic, the defending champion and World No. 1, was ready for another battle.
The opening set went to Djokovic, clinched in a tense tiebreak. Wawrinka struck back in the second, and the third became a knife fight — Wawrinka pushing ahead, Djokovic clawing back, until the Swiss broke serve late to move within one set of the title. In the fourth, Wawrinka closed with brilliance. Precision off both wings, fearless backhands skimming the lines, and relentless aggression left Djokovic chasing shadows.
Wawrinka sealed the match 6–7, 6–4, 7–5, 6–3, earning a heartfelt embrace from the champion he had just dethroned. It was his third Slam in three years, proof that on his day, the quiet Swiss could shake even the mightiest throne.
If there’s one player who perfectly embodies the Sandwich Generation — and whose recent struggles we’ve witnessed, bowing out in the first round of the 2025 US Open — it’s Daniil Medvedev. Born in Moscow and based in Monaco, Medvedev has always been capable of reaching extraordinary heights. He has contested six Grand Slam finals (four against Djokovic, two against Nadal), captured six Masters 1000 titles, and in February 2022 became World No. 1 — just before Sinner and Alcaraz began outplaying him.
But rewind to 2021, when Djokovic was chasing immortality. The Serbian had already won the Australian Open, Roland Garros, and Wimbledon, arriving in New York with a chance to complete the calendar Grand Slam. Standing in his way was the world’s No. 2, Medvedev. That night in Arthur Ashe, the Russian delivered the performance of his life. He broke Djokovic early and took the first set 6–4 behind immaculate serving. He repeated the scoreline in the second, his flat forehand driving through the court and keeping Djokovic on the back foot. Suddenly, Medvedev was one set away from his first major, and Djokovic’s dream was crumbling. Even as the champion tried to summon a fightback, Medvedev was unshakable. On his third championship point, he unleashed a 129mph serve, sealing a straight-sets victory: 6–4, 6–4, 6–4. In just over two hours, he denied Djokovic’s bid for history and claimed his first Grand Slam title — a triumph that defined his career.
2014 was one of the most contested years for the Big Three. Stan Wawrinka had stunned Nadal to win the Australian Open and later that season, the US Open produced something unseen since 2005: a Grand Slam final without Federer, Nadal, or Djokovic. Nadal was sidelined with a wrist injury, Federer fell to Marin Cilic in the semifinals 6–3, 6–4, 6–4 and Kei Nishikori ousted Djokovic on the other side of the draw 6–4, 1–6, 7–6^(7–4), 6–3.
For the first time, the US Open would feature an Asian player in the final — and a Croatian who had just returned from a 2013 doping ban. In the championship match, Cilic delivered the performance of his life. Behind booming serves and relentless baseline hitting, he overpowered Nishikori 6–3, 6–3, 6–3 to claim his maiden Slam. With it, he became Croatia’s first US Open champion, etching his name into the history of Flushing Meadows and Croatian sports history.
As we head into the final week of the 2025 US Open, one question lingers: will this year’s tournament deliver yet another upset?
