Top five biggest upsets in US Open history feat. Roger Federer, Novak Djokovic & more

Roger Federer is the only male tennis player to defend his title at the US Open in the 21st century.

Tennis enthusiasts and former players often see the US Open as one of the most unpredictable tournaments. Interestingly, we have witnessed several tournament champions in the last two decades. Played during the North American swing, the US Open takes place in New York.

Even the likes of Rafael Nadal and Novak Djokovic have failed to defend their titles in Flushing Meadows. Moreover, the Grand Slam has been a hub of upsets and surprising results. Thus, without further ado, let’s take a look at the top five biggest upsets in US Open history:

5. Novak Djokovic vs Alexei Popyrin: 2024

The defending champion of the US Open, Novak Djokovic, suffered a disappointing loss against Australia’s Alexei Popyrin in the third round of the 2024 US Open. After an upsetting season, the Serb arrived at Flushing Meadows with an Olympic gold medal. However, Djokovic failed to get the better of Popyrin, who won in four sets.

As a result of Djokovic’s loss, no player of the ‘Big 3’ will be a part of the fourth round of a Grand Slam since 2022. Against Popyrin, Djokovic made 16 double faults and converted five breakpoints out of the 12 opportunities he had. For some, it’s the official end of the ‘Big 3’.

4. Carlos Alcaraz vs Botic van de Zandschulp: 2024

Third seed Carlos Alcaraz lost to the Netherlands’ Botic van de Zandschulp in straight sets in the second round of the 2024 US Open. Alcaraz, who won the Wimbledon Championships, Roland Garros and an Olympic silver medal, before stepping into the North American swing.

Returning to Cincinnati, he lost to Gael Monfils in the second round. After the loss, the Spaniard lost his cool and broke his racquet by smashing it on the ground. His struggles continued at Flushing Meadows as he lost to Zandschulp in the second round 6-1, 7-5, 6-4. Throughout the match, the four-time Grand Slam champion looked puzzled. However, after the loss, he gave the match his flowers and stated that he wasn’t able to step up his game.

3. Marin Cilic vs Roger Federer: 2014

The last male tennis player to defend his title at Flushing Meadows, Roger Federer lost to Marin Cilic in the semi-finals of the 2014 US Open. Second set Federer lost to Croatia’s Cilic in straight sets, which was a huge upset. Coming from a loss in the Wimbledon final against Novak Djokovic, the Swiss Maestro was not enjoying a comfortable campaign in New York.

Cilic was a heavy underdog at Flushing Meadows in 2014. However, he went on to win the title by stunning Roger Federer in the semifinals and Kei Nishikori in the final. The final of the tournament was expected to be a clash between the top two seeds, Djokovic and Federer. However, the tables turned in the final as both of them lost against lower-seeded opponents.

2. Serena Williams vs Roberta Vinci: 2015

Serena Williams was only one step away from adding another chapter of greatness to her illustrious tennis career. However, Roberta Vinci came in her way and won the 2015 US Open women’s singles semi-final. Unseeded Roberta Vinci, who never reached the quarterfinals of any Grand Slam in singles competitions, excelled at Flushing Meadows.

She faced her toughest challenge as Serena Williams awaited her in the semifinals. In 2015, Williams was chasing a Calendar Slam, which is one of the rarest feats in tennis. After winning the initial three Grand Slams of the season, it seemed like she would complete a Calendar Slam comfortably. However, Roberta Vinci didn’t allow Williams to win.

1. John Millman vs Roger Federer: 2018

Known for consistency and flair, Roger Federer lost to a player outside the top 50 rankings for the first time during the 2018 US Open. He suffered a disappointing 3-6, 7-5, 7-6 (7), 7-6 (3) loss against Millman in the fourth round of the 2018 US Open. The five-time champion got tough competition against Millman, eventually resulting in an upsetting fourth-round exit in New York.

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