From Rafael Nadal losing to Robin Soderling, Novak Djokovic falling to Denis Istomin to Carlos Alcaraz's shock loss to Botic Van de Zandschulp: 8 biggest men's Grand Slam upsets in the last 15 years
Rafael Nadal and Novak Djokovic have both been on the receiving end of some of the biggest Grand Slam upsets in men's tennis over the past 15 years. While the two have dominated the sport for a long time, they've also had their fair share of forgetful moments at Majors.
Carlos Alcaraz recently suffered a disastrous exit in the second round of the 2024 US Open after losing to Botic van de Zandschulp in straight sets. This is the only time the Spaniard failed to reach the quarterfinals or beyond at a Grand Slam in this season.
Apart from Alcaraz, there have been a number of instances when some of the best tennis players have suffered early-round exits at Majors to unheralded opponents.
On that note, let us take a look at the eight biggest men's Grand Slam upsets in the last 15 years.
#8 Carlos Alcaraz vs Botic van de Zandschulp - US Open 2024
Although Carlos Alcaraz entered this year's US Open at the back of a second-round exit in Cincinnati, the 21-year-old was still among the heavy favorites to win, having previously clinched the previous two Grand Slams at Wimbledon and the French Open.
Alcaraz did not have the strongest of starts to the New York Major as he took four sets to beat Australian qualifier Li Tu. The third-seeded Spaniard then took on World No. 74 Botic van de Zandschulp, who had won just four out of 13 main-draw matches on hard-courts this season ahead of the US Open.
The Dutchman produced a sensational performance to script what might go down as the biggest upset of the tournament, as he beat Alcaraz 6-1, 7-5, 6-4. This was the Spaniard's worst Grand Slam finish since losing in the second round of Wimbledon 2021.
#7 Rafael Nadal vs Lukas Rosol - Wimbledon 2012
Rafael Nadal played one grass-court tournament before Wimbledon 2012 at Halle, where he suffered a quarterfinal exit. The Spaniard was seeded second at the tournament and started strongly with a 7-6(0), 6-2, 6-3 win over Thomaz Bellucci.
Nadal faced then-World No. 100 Lukas Rosol in the second round and took the lead in the match by taking the first set via a tiebreak. However, the Czech bounced back and took the next two sets 6-4, 6-4 to tilt the scales in his favor.
Nadal then dominated the fourth set and won it 6-2 to force the match into a decider, which Rosol eventually won 6-4 to script a Wimbledon upset for the ages. This remains the Czech's only win against the 22-time Grand Slam champion.
#6 Roger Federer vs Andreas Seppi - Australian Open 2015
Roger Federer started the 2015 season well by winning the Brisbane International, during which, he registered the 1000th win of his career. The Swiss then competed at the Australian Open as the second seed and started with a straight-set win over Lu Yen-hsun (6-4, 6-2, 7-5) before coming back from a set down to beat Simone Bolelli (3-6, 6-3, 6-2, 6-2).
Federer faced then-World No. 46 Andreas Seppi in the third round and found himself two sets down. The then-33-year-old showed some resilience and took the third set before the Italian clinched the fourth set via a tiebreak to register a 6-4, 7-6(5), 4-6, 7-6(5) win.
This defeat put an end of Federer's streak of 11 consecutive semifinal appearances at the Australian Open.
#5 Novak Djokovic vs Denis Istomin - Australian Open 2017
Novak Djokovic had a good start to the 2017 season by winning the Qatar Open. He then competed at the Australian Open, where he was the two-time defending champion.
The Serb booked his place in the second round of the Melbourne Major with a 6-1, 7-6(4), 6-2 win over Fernando Verdasco. He then faced Denis Estomin, who was ranked 117th in the world at the time and needed a wildcard to enter the main draw.
The first set was closely contested, with the Uzbek triumphing via a tiebreak, but Djokovic did well to win the next two sets 7-5, 6-2. However, Istomin edged out the Serb via a tiebreak to take the fourth set and force the match into a decider. The Uzbek then won the final set to register a 7-6(8), 5-7, 2-6, 7-5(5), 6-4 and handing Djokovic his worst Grand Slam finish since losing in the second round of Wimbledon in 2008.
#4 Roger Federer vs Sergiy Stakhovsky - Wimbledon 2013
Federer entered Wimbledon 2013 after winning his first title of the season in Halle. The Swiss was the defending champion at the grass-court Major and was seeded third.
He started the tournament by thrashing Victor Hanescu 6-3, 6-2, 6-0 and setting up a second-round clash against then-World No. 116 Sergiy Stakhovsky. All four sets were tightly-contested, with Federer winning the first one before the Ukrainian took the next three to register a 6-7(5), 7-6(5), 7-5, 7-6(5) win.
The Swiss thus suffered his worst Grand Slam finish since the 2003 French Open.
#3 Rafael Nadal vs Steve Darcis - Wimbledon 2013
Rafael Nadal entered Wimbledon 2013 at the back of a 22-match winning streak, that included winning that year's French Open and two Masters 1000 events in Madrid and Rome.
The Spaniard was seeded sixth at the grass-court Major and his first-round opponent was then-World No. 135 Steve Darcis.
Darcis produced some fine tennis to take a two-set lead in the match after narrowly winning both sets via a tiebreak. The Belgian then took the third set 6-4 to hand Rafael Nadal his very first opening-round defeat at a Grand Slam.
#2 Novak Djokovic vs Sam Querrey - Wimbledon 2016
Novak Djokovic had already won six titles in 2016 before Wimbledon. This included winning the Australian Open and the French Open.
The Serb booked his place in the third round of the grass-court Major after straight-set wins over James Ward and Adrian Mannarino. Here, he faced 28th seed Sam Querrey, and the American had a stranglehold on the match after winning the first two sets 7-6(6), 6-1.
Djokovic kept his hopes alive in the match after taking the third set. The fourth set went to a tiebreak but Querrey narrowly won it to secure a 7-6(6), 6-1, 3-6, 7-6(5) win and end the Serb's streak of four successive Grand Slam wins.
#1 Rafael Nadal vs Robin Soderling - French Open 2009
This match will forever be remembered as one of the greatest upsets in tennis history, if not the greatest, like almost any other match that Rafael Nadal lost at the French Open.
The Spaniard entered the 2009 edition of the clay-court Major as the four-time defending champion. At the time, he had also won the Monte-Carlo Masters and the Italian Open, while also reaching the final of the Madrid Open.
Nadal reached the fourth round of the 2009 French Open following straight-set wins over Marcos Daniel, Teymuraz Gabashvili and Lleyton Hewitt. Here, he faced 23rd seed Robin Soderling.
The Swede got off to a fine start and won the first set 6-2 before Nadal bounced back to take the second via a tiebreak and level the match. However, Soderling was not to be denied and he eventually registered a 6-2, 6-7(2), 6-4, 7-6(2) win to hand the Spaniard his very first defeat at the French Open.
This remains the only time the Swede beat Nadal on clay.