Top 10 biggest upsets in Grand Slam history

The ATP, WTA Tours have occasionally seen lower-ranked players cause major upsets at Grand Slams.

It’s a natural tendency to root for the underdog. A rank outsider getting the better of the clear favourite is something that reinforces interest in the game and keeps the crowds coming back for more.

Former and current champions such as Roger Federer, Novak Djokovic, Rafael Nadal, and Serena Williams rely on their ability to bounce back even when times are tough. But on the odd occasion, even the underdogs have their moment in the sun.

The individual in question could be a rookie player or a wily veteran who showcased their best performances to upset the champions. Such unforeseen results always generate a lot of buzz, resulting in captivating match-ups. For that is how legends are born and new talent is unearthed.

Here are some of the Cinderella stories of the Grand Slams that threw up the most unthinkable results in tennis and sporting history.

Biggest Grand Slam upsets-

10. Mark Philippoussis defeats Pete Sampras – 1996 Australian Open

When Philippoussis took on Pete Sampras in the 1996 Australian Open in the third round, he was ranked 40th. He was a 19-year-old taking on the World No. 1. Sampras was also the reigning Wimbledon and US Open Champion. 

The win by Philippoussis over Sampras was a shot in the arm for Australian tennis and the first by an Aussie over a No. 1 since Pat Cash defeated Ivan Lendl in the 1988 edition of the Australian Open. The young Australian overpowered Sampras in straight sets, 6-4, 7-6(9), 7-6(3) in the floodlit Rod Laver Arena.

Also Read: Top five youngest-ever match winners on ATP Tour men’s singles

9. Richard Krajicek defeats Pete Sampras – 1996 Wimbledon

Until Richard Krajicek defeated Pete Sampras in the 1996 Wimbledon quarter-finals, the American had assumed ownership of the grass courts at SW19. Sampras won seven Wimbledon titles between 1990 and 2002, including four on the trot between 1997 and 2000, to add to the three SW19 trophies won between 1993 and 1995. 

The only time he lost the title between those years was to outsider Richard Krajicek, the Dutchman who overcame the then three-time champion 7-5, 7-6(3), 6-4 in three sets.

Krajicek went on to defeat another American, Malivai Washington, for a 6-3, 6-4, 6-3 win, capping a dream run that gave him his only Grand Slam trophy. 

8. Goran Ivanisevic defeats Patrick Rafter –  2001 Wimbledon

When Goran Ivanisevic lifted the 2001 Wimbledon trophy, he was only the second unseeded player to do so, the first being Boris Becker in 1985. By 2001, the left-handed Croatian had made it to three SW19 finals. Ranked a lowly No. 125, Ivanisevic was given a wildcard entry into the tournament. In 1998, he lost his third trip to the Wimbledon final, and for the second straight time to Pete Sampras.

On the way to his 2001 title run, Ivanisevic defeated No. 3 Marat Safin in four sets and ended British hopes of a home champion by overcoming Tim Henman in five. The title round saw 2000 finalist and two-time US Open champion, Patrick Rafter, against Ivanisevic.

The Croatian overcame the World No. 10 Rafter in a marathon five-setter, 6-3, 3-6, 6-3, 2-6, 9-7 to taste Grand Slam and Wimbledon success for the first time. 

7. Sam Stosur defeats Justine Henin & Serena Williams – 2010 French Open

Sam Stosur made the headlines in 2010 at Roland Garros by scoring a double upset. First, she defeated four-time French Open champion Justine Henin in the fourth round, 2-6 6-1 6-4 to end the Belgian’s 24-match winning streak at Roland Garros. Her next victim was the 2002 winner, Serena Williams, also in three sets, 6-2, 6-7(2), 8-6.

Stosur carved out a place in the history books for herself when she made the finals, becoming the first Australian woman to advance to a major singles final in 30 years. Wendy Turnbull achieved the feat in 1979.

Stosur, however, came up short in the final against Francesca Schiavone, a 29-year-old Italian also contesting her first major final. Schiavone became the first Italian woman to win a Grand Slam with a 6-4, 7-6(2) victory. The Australian made amends for the loss with a win over Serena in the 2011 US Open final to win her first major singles title.

6. Marin Cilic defeats Roger Federer – 2014 US Open

After Kei Nishikori did Federer a favour by knocking out the 2011 US Open champion Novak Djokovic in their semi-final match, it was left to the Swiss great to fill the spot as favourite and pick up his sixth US Open title. Federer was fresh from winning the Cincinnati Open earlier that month and was leading Cilic 5-0 in their head-to-head.

The Croatian was in only his second Grand Slam semi-final. However, Cilic scripted the best performance of his career, cruising past Federer for a convincing 6-3, 6-4, 6-4 victory. Cilic went on to lift the title, his only Grand Slam win and sole win against Roger Federer.

Also Read: Top five oldest men’s singles Grand Slam champions

5. Roberta Vinci defeats Serena Williams – 2015 US Open

When Serena Williams walked onto Arthur Ashe Stadium, she was close to achieving one of the rarest records in tennis – a calendar slam. Williams would have become the first singles player to do so since Stefanie Graf in 1988. Instead, she saw her 33-match win streak at the majors come to an end. That journey included trophies from Melbourne, Roland Garros, Wimbledon, and the 2014 US Open.

The 32-year-old unseeded Vinci, who had lost four previous matches to the American, pulled off an epic win over the then World No. 1 in three sets, 2-6, 6-4, 6-4. in the semi-finals The outcome was the first all-Italian singles final in the Open Era, in which Vinci finished as runner-up to Flavia Pennetta.

4. Mischa Zverev defeats Andy Murray – 2017 Australian Open

Murray was the World No. 1 during the 2017 Australian Open. He did not drop a set in the first three matches in Melbourne and looked sharp on the court. In the fourth round, he set up a clash against German Mischa Zverev, who was ranked World No. 50. The elder brother was known for his powerful serve and avoided baseline rallies.

Murray was not able to overcome Zverev’s strategy. His serve was broken nine times in the match as Zverev took the opening set. Murray fought back in the next to level the scores; the crowd thought it would be a slight hiccup in the top seed’s campaign.

But it turned out to be the end of Murray in the event as he lost the next two sets. Zverev defeated Murray 7-5, 5-7, 6-2, 6-4 in three hours and 30 minutes. It was Murray’s earliest exit in Melbourne since 2009 when he lost in the fourth round to Fernando Verdasco.

3. Linda Noskova defeats Iga Swiatek – 2024 Australian Open

Czech teen Linda Noskova handed World No. 1 Iga Swiatek her earliest exit at Melbourne since the 2019 season. Swiatek headed for the exit in the 3rd round. In 2019, she went to the second round. The Pole took the lead after winning the first set, but Noskova fought back for a 3-6, 6-3, 6-4 on Rod Laver Arena.

Noskova, ranked No. 50 in the season’s opening Grand Slam, is the lowest-ranked player to defeat Swiatek in Melbourne yet. With the win, Noskova reversed the result from their earlier meeting in Poland in July 2023 and ended Swiatek’s 18-match unbeaten streak, which stretched back to September.

2. Robin Soderling defeats Rafael Nadal – 2009 French Open

In 2009, the Swedish journeyman Robin Soderling scored a win over Rafael Nadal on his preferred stomping grounds at Roland Garros.  It was the Spaniard’s first loss in five trips to Paris, and only a few weeks after taking down Soderling 6-1, 6-0, a few weeks earlier in Rome.

The 6-2, 6-7(2), 6-4, 7-6(2) win in the fourth round was one of the finest moments of Robin Soderling’s career and the biggest shock in the tournament’s recent history. Nadal was on a roll at Roland Garros, having won four straight French Open trophies, and was on a 31-match winning streak at the venue.

Nadal’s loss cleared the way for Soderling to make his first Grand Slam final and for Federer to win the only major eluding his grasp – the French Open.

1. Alexei Popyrin defeats Novak Djokovic – 2024 US Open

Alexei Popyrin was responsible for the second upset in as many days by sending the defending champion, Novak Djokovic, home early in Flushing Meadows. Earlier, Botic van de Zandschulp had eliminated 2022 champion Carlos Alcaraz in the second round.

Popyrin made the trip to New York with newfound confidence after winning the Montreal Masters. His win in Montreal saw him defeat three top ten players en route to his maiden ATP 1000 title.

The Australian had extended Djokovic in their previous two meetings in Grand Slams to four sets –  the 2024 Australian Open and Wimbledon. The upset was in the works, with the Serb’s only bright spot being the Olympic Gold this season.

The third-round exit by Djokovic following the 6-4, 6-4, 2-6, 6-4 loss meant the Serb will end a season without a Grand Slam win for the first time since 2017.

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