Most shocking Wimbledon upsets of 21st century ft. Serena Williams-Alize Cornet, Rafael Nadal-Dustin Brown and more

Rafael Nadal and Serena Williams are among the biggest names in tennis and are multi-time Wimbledon champions. The latter has won the tournament on record seven occasions in the 21st century.

But when you make such a big name for yourself, the losses also make big news. And both Nadal and Serena Williams have fallen prey to shock defeats at the All England Club.

Inspired underdogs are always looking to make a statement by beating the big guns, and what better stage to do it than at the home of tennis — Wimbledon itself. With the 2025 edition of the tournament just around the corner, let’s jog up memories of some of the biggest shocks that have unfolded at the grasscourt Slam this century:

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#7 George Bastl defeated Pete Sampras (2002 Wimbledon)

Pete Sampras at the 2002 Wimbledon. (Source: Getty)

Pete Sampras had come into the 2002 Wimbledon Championships not having won a title for over a year and a half. Solid showings on the Tour, however, ensured that he was among the top seeds at the tournament that he had won on seven prior occasions.

The American began the tournament in dominant fashion, coming through in straight sets against local player Martin Lee. He was the heavy favorite to win his second-round encounter against lucky loser George Bastl, but the Swiss player had other plans.

Bastl showed incredible fighting abilities to prevail over a much fancier opponent in a match characterized by giant momentum swings. He came through 6-3, 6-2, 4-6, 3-6, 6-4 for the biggest win of his career. The fact that it was Sampras' last match at the All England only added value to the upset's lore.

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#6 Tsvetana Pironkova defeated Venus Williams (2010 and 2011 Wimbledon)

Tsvetana Pironkova at the 2011 Wimbledon (Source: Getty)

Tsvetana Pironkova was a grasscourt rookie back in 2010, with a lackluster 1-4 record at the Wimbledon Championships. Her pacey, flat backhand, nifty forehand slice and big serve, however, wreaked havoc in the draw.

By the time the Bulgarian reached the quarterfinals, she was exuding confidence. But a titanic tussle awaited her in the form of five-time former champion Venus Williams. She, however, showed the packed crowds that the lush lawns at SW19 were as well-suited for her unconventional game as for Venus' power-heavy brand of tennis.

Pironkova outmaneuvered, outserved and at times outhit her opponent from the baseline in a sublime display of grasscourt finesse. "I'm surprised by how quick it was," Pironkova said of her 6-2, 6-3 win, a little shocked at just how effective her low-bouncing shots were beginning to feel on grass. The fact that she repeated the result with the exact same scoreline against Venus a year later the 2011 Championships, is another story altogether.

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#5 Michelle Larcher de Brito defeated Maria Sharapova (2013 Wimbledon)

Michelle Larcher de Brito at the 2013 Wimbledon. (Source: Getty)

The Wimbledon 2003 second-round encounter between Michelle Larcher de Brito and Maria Sharapova is recalled most often for its decibel value. Amid the loud grunts from both ends of the court, however, there lay plenty of other stories.

Larcher de Brito, for starters, was flying the flag high for Portuguese tennis as just the second woman competing at the Grand Slam stage. The third-seed Sharapova herself was in a very good position, having made the finals of the last five tournaments (including the French Open) that she had played and won two of them.

It was a battle royale from the baseline, one that eventually swayed in favor of the underdog. De Brito played out of her skin, while untimely slips and uncharacteristically poor serving saw Sharapova unravel and submit to a 6-3, 6-4 loss.

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#4 Sam Querrey defeated Novak Djokovic (2016 Wimbledon)

Sam Querrey and Novak Djokovic at the 2016 Wimbledon Championships. (Source: Getty)

Sam Querrey's big serve was a certified weapon for grass on any given day. The big day arrived at the 2016 Wimbledon Championships when he found himself up against top seed Novak Djokovic.

Not only was Djokovic the top-ranked player, but also the two-time defending champion. To top that, he has won both the Australian Open and French Open that year and was still on course for a Calendar Slam. None of that mattered in the end as he was second best on the court that day.

Queerey hit 31 aces in the four-set battle against Djokovic, also breaking his opponent’s serve on four occasions. The 7-6(6), 6-1, 3-6, 7-6(5) win was bookended by two tiebreaker sets in a classic big server fashion.

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#3 Alize Cornet defeated Serena Williams (2014 Wimbledon)

Alize Cornet (Source: Getty)

Alize Cornet was by no means new to the big stage when she played Serena Williams at the 2014 Wimbledon Championships. Up against the World No. 1 and multi-time former champion, though, she was a heavy underdog.

The Frenchwoman’s game was also not the best-suited for grass, but she showed that if you hang around in rallies long enough, even the best will begin to falter. She did not allow Serena to settle into a rhythm, constantly mixing up the shot selection to keep her opponent guessing.

Cornet had plenty of grass matches under her belt and made the best of her experience. She used the slice, dropshot and came into the net every chance she got — including hitting a standout 360-turn no-see volley at 3-0 (*15-30) in the second set. The variety and enterprising tennis helped her eke out a memorable 1-6, 6-3, 6-4 win.

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#2 Dustin Brown defeated Rafael Nadal (2015 Wimbledon)

TENNIS: JUL 02 Wimbledon - Source: Getty

Dustin Brown had a certain exuberance about him when he played Rafael Nadal at the 2015 edition of the major in London. He had not stepped out on a court this grand or a crowd this big, but he looked like he belonged.

The German-Jamaican player had come through qualification rounds and won a match in the main draw to set up the second-round meeting. The world had gotten a glimpse of his dynamic brand of tennis, but no one was prepared for the bag of tricks that he brought to court that day.

Brown was hitting 125 mph second serve aces, drop shot return winners, improbable volleys and Nadal was left, well, scrambling for answers. Eventually, the former champion was outplayed. Brown hit 71 winners compared to Nadal’s 46 en route to the 7-5, 3-6, 6-4, 6-4 win.

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#1 Sergiy Stakhovsky defeated Roger Federer (2013 Wimbledon)

Sergiy Stakhovsky sits with his head covered as Roger Federer walks by his side. (Source: Getty)

The image of Sergiy Stakhovsky sitting with his head buried in his towel as Roger Federer walks off Centre Court says almost everything you need to know about this match. The shock value was huge, even for the winner himself.

The seven-time champion was expected to cruise through the second-round encounter. He fairly moved into a lead after a tight opening set as two sublime single-handed backhands went toe-to-toe on the biggest stage of tennis.

Don’t get this wrong, Federer was playing great tennis. It was Stakhovsky who suddenly raised his level and was even more ferocious with his groundstrokes and net approaches, which were critical in winning him big points.

In telling stats, the Ukrainian, who who never beaten a top-10 player in 20 attempts, hit 20-plus more winners and one more ace than Federer, outclassing the man who was arguably the most difficult to beat at the All England Club.