3 of the Biggest Upsets at Tennis Grand Slams Ever

Explore three of the biggest Grand Slam tennis upsets, from Soderling shocking Nadal to van de Zandschulp beating Alcaraz and Stakhovsky stunning Federer.

Often, at least two or three of the top four seeds at the Grand Slams – Australian Open, Roland Garros, Wimbledon, and US Open – make it to the semi-finals. And very often, one of those stars wins the tournament. But sometimes there’s a big shock that fans remember decades later.

Robin Soderling beats Rafa Nadal

At the 2009 French Open, surely there would only be one winner between Robin Soderling and Rafa Nadal. The latter was the undisputed world’s best player on clay; he hadn’t ever lost at Roland Garros. A few weeks before this match, Soderling had almost double-bagled Nadal, winning 6-0, 6-1, so the warning signs were there. But Nadal was still the overwhelming favourite and, if it wasn’t for this loss, might have won 10 straight French Opens. (His run of titles was interrupted by Roger Federer, who beat Soderling in the final that year.)

Before 2009, Nadal had beaten Federer in three straight Roland Garros finals, with Federer never getting more than a set. And before that, Nadal beat Mariano Puerta for his first title. Martina Navratilova, winner of an Open Era record 59 Slam titles (18 in singles), said Soderling’s win over Nadal was one of the biggest upsets in tennis history.

Botic van de Zandschulp beats Carlos Alcaraz

Ahead of the 2024 US Open, Carlos Alcaraz was favourite for the men’s singles title. His opponent in the second round was a previous Slam quarter-finalist but had been struggling so much of late that he had considered retirement. Amazingly, van de Zandschulp won in straight sets in a career-best match, beating the player who had won the previous two Slams.

Over the last two-to-three years, Alcaraz and Sinner have dominated the sport and won the last 9 Grand Slam between them. But Alcaraz is slightly less consistent than Sinner – it is generally thought that his highest level is better, with even Sinner struggling to stay with him on his best day, but his lowest level is lower. Sinner is almost robotically consistent, having recently become the first male player to win five straight Masters 1000 tournaments.

On the 10bet.co.za app for iOS, Alcaraz and Sinner lead the way in outrights Wimbledon winner betting. Even players like Novak Djokovic and Alexander Zverev are considered underdogs at around 8/1 and 16/1.

Van de Zandschulp has since had mixed results and is currently outside the top 40. He had a decent tournament in the Bucharest 250, but fell to world No 60 Mariano Navone. The Dutchman’s best result this year was arguably beating Denis Shapavalov in Miami – not a shock on the scale of the Alcaraz win, but something to celebrate nonetheless.

Sergiy Stakhovsky beats Roger Federer

Roger Federer had made at least the quarter-finals of Wimbledon every year since 2003 when he met Sergiy Stakhovsky in 2013. The latter, almost unbelievably, won in straight sets – and then never made it past the third round of any Slam in his career. Federer had won his sixth title at Halle in seemingly perfect preparation on the grass. But a closer look at the details suggests there were some signs of vulnerability: Federer dropped a set against Mikhail Youzhny in the Halle final, having previously won all 14 matches against him. And Federer, then 31 years old, had already had back injuries earlier that year.

When the pair met at Wimbledon, Federer had won 13 grass titles, and Stakhovsky had won a combined 12 grass matches. But early on, it was clear the Ukrainian was having a good day: he attacked the net early and ended the match with 96 moves forward. He mixed up the rhythm with volleys, chips and charges, slices, and heavy groundstrokes.

When Federer miscued a backhand down the line on match point, the Ukrainian fell to his back in celebration, legs kicking the air like a happy baby. It was called one of the most “incredible” days at SW19.

Stakhovsky finished his career with 177 wins and 215 defeats. His highest ATP ranking was No 31, achieved three years before his defeat of Federer. The Ukrainian was ranked 116 at the time of that match, and Federer had reached 36 consecutive quarter-finals at Grand Slams. Due to the crowd’s support for Federer, Stakhovsky said it was like “playing two people”.

Federer went on to win a total of eight Wimbledon titles and competed in 12 finals. He called it his favourite tournament. His 2008 clash with Nadal, one of the few finals Federer lost, is considered one of the all-time great tennis matches.