Where Does Alcaraz’s Loss Rank In Men’s Tennis’ Most Shocking Upsets Of The 21st Century?

Carlos Alcaraz ahead of ATP Madrid

One of Rafael Nadal’s time-tested propositions was, “On any given day, in any tournament, any player qualified to be in the ATP is capable of beating any other ATP player.” Over the 24 years of this century, there have been many crazy upsets which no one saw coming. As Nadal said, it could and would eventually happen over time to the best of the players. And it did to Carlos Alcaraz.

Botic van de Zandschulp played the best match of his life to defeat Carlos Alcaraz in what was the biggest upset of the year and one of the biggest of all time. He was solid throughout the match and made it difficult for Alcaraz to hit past him. He came to the net more than Alcaraz, who was very one-dimensional.

Of course, the biggest upset of the century was probably at the very beginning, when Lucky Loser George Bastl took out seven-time champion and #6 seed Pete Sampras in the second round of Wimbledon in 2002. The rise of the “Big Four” era started shortly after that, and stunning upsets came few and far between. They still happened, though, which make them all the more exciting. So where does Alcaraz’s upset rank among them?

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Top 5 Upsets of the 21st Century

5. Lukas Rosol (#100) def. Rafael Nadal (#2), 2012 Wimbledon, Second Round

Lukas Rosol defeated Rafael Nadal in five sets in the second round of Wimbledon. At the time this was a monumental shock seeing that Nadal had made five consecutive Wimbledon finals (missed 2009 due to injury) and had just won the French Open final against Novak Djokovic. After this loss, Nadal lost to players outside the Top 100 for three consecutive years at Wimbledon. So in hindsight, it does not seem that shocking but it certainly was at the time.

4. Botic van de Zandschulp (#74) def. Carlos Alcaraz (#3), 2024 US Open, Second Round

Botic van de Zandschulp stunned the tennis world as he beat Carlos Alcaraz in straight sets. This was Alcaraz’s worst loss at a Grand Slam since his first Grand Slam appearance at the 2021 Australian Open, as a qualifier. The Spaniard had won the last two Slams and was the favorite to win the US Open. Van de Zandschulp has been a quarterfinalist before at a Slam but what makes this so shocking is that he had been in the worst form of his life and was considering retirement from tennis a couple of months back. It is undoubtedly the biggest upset of this decade, and its significance might increase or decrease with time.

3. Sergiy Stakhovsky (#116) def. Roger Federer (#3), 2013 Wimbledon, Second Round

Roger Federer, the King of Grass, the defending champion at the time, who had made the quarterfinals of Wimbledon every year since 2003, was shocked by the Ukrainian, Sergiy Stakhovsky. Yes, Federer had a rather poor 2013 by his standards but had still reached the Australian Open semifinal, losing a close match to Andy Murray, reached the Rome final, won Halle, and was looking in good grass form until this result happened where Federer lost in four sets. Stakhovsky never made it past the third round of a Grand Slam in his career. This loss still makes no sense.

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2. Denis Istomin (#117) def. Novak Djokovic (#2), 2017 Australian Open, Second Round

Two-time defending Australian Open champion at the time, who had won the Australian Open for five of the past six years, lost in five sets to Uzbek Denis Istomin in his most dominant court. Istomin was trailing two sets to one and made the biggest comeback of his career. Djokovic did not have a particularly good 2017 but he still made the quarterfinals of the French Open and Wimbledon before missing the rest of the year due to injury. Before this, he had won the Australian Open and reached the US Open final in 2016. He also beat the then-World No.1, Andy Murray, at the start of 2017 so this result was a complete shocker.

1. Robin Soderling (#25) def. Rafael Nadal (#1), 2009 French Open, Fourth Round

This is the single biggest tennis upset of the century and one of the biggest upsets in sports history. It might not look like that on paper, especially if you are a new tennis follower, but nothing shocked the tennis world quite like this. Rafael Nadal hadn’t lost to anyone ever at the French Open and it was believed that he would never lose a match there in his 20s. Soderling had been beaten 6-0 6-1 by Nadal a few weeks before the match. But he ended up beating the Spaniard in four sets.

Nobody even expected him to take more than three games in a set heading into that match. Nadal could have been able to win 10 consecutive Roland Garros titles if there hadn’t been this upset. This also allowed Roger Federer to capture his one and only French Open title. However, Soderling did go on to become a good clay courter and reached the Top 5 in rankings. But in the context of expectations going into the match and what he’d achieved to that point, this was the most monumental upset of the century.

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Notable Mentions

Andreas Seppi (#46) def. Roger Federer (#2), 2015 Australian Open, Third Round

Sam Querrey (#41) def. Novak Djokovic (#1), 2016 Wimbledon, Third Round

Mischa Zverev (#50) def. Andy Murray (#1), 2017 Australian Open, Fourth Round

Steve Darcis (#135) def. Rafael Nadal (#5), 2013 Wimbledon, First Round

Main Photo Credit: Geoff Burke-USA TODAY Sports

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