16 Wimbledon Upsets That Stunned Tennis Fans
Wimbledon has always been tennis’ most prestigious tournament, where legends are born and history gets written. But sometimes the script gets flipped completely, and unknown players shock the world by beating established champions. These moments make us remember why we fell in love with tennis in the first place.
The grass courts at the All England Club have seen their share of jaw-dropping surprises over the years. Here is a list of 16 Wimbledon upsets that left everyone speechless.
Lleyton Hewitt Loses in First Round (2003)
Defending champion Lleyton Hewitt walked onto Centre Court as the tournament’s top seed, ready to begin what should have been a routine title defense. Croatian Ivo Karlovic had different plans entirely.
The 6’10” giant served his way to a stunning 1-6, 7-6, 6-3, 6-4 victory, making Hewitt the first defending men’s champion to lose in the opening round. Hewitt later admitted he’d never even watched Karlovic play before their match.
Rafael Nadal Falls to Steve Darcis (2013)
Rafael Nadal arrived at Wimbledon fresh off his eighth French Open title, looking dangerous on any surface. Belgian Steve Darcis, ranked 135th in the world, wasn’t intimidated by the occasion or the opponent.
The left-hander played brilliant tennis to defeat Nadal in straight sets on Court 1, sending the Spaniard home after just one match. This upset ranks among the most shocking first-round exits in tournament history.
Lukas Rosol Stuns Rafael Nadal (2012)
Czech qualifier Lukas Rosol entered his match against Rafael Nadal with nothing to lose and everything to gain. The 100th-ranked player unleashed the performance of his lifetime, attacking from the baseline and never backing down.
Rosol’s fearless approach completely overwhelmed the two-time Wimbledon champion, leading to a four-set victory. The Czech celebrated like he’d just won the entire tournament, which for him was probably more meaningful than any title.
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Dustin Brown Defeats Rafael Nadal (2015)
German qualifier Dustin Brown brought his unique style to Centre Court and gave Rafael Nadal fits for an entire afternoon. Brown’s unorthodox approach included drop shots, net rushes, and angles that left Nadal scrambling.
The German’s 7-5, 3-6, 6-4, 6-4 victory proved that unpredictability can be the best weapon against even the greatest players. Brown’s dreadlocks and entertaining style made him an instant fan favorite.
Serena Williams Loses to Alizé Cornet (2014)
Serena Williams entered Wimbledon 2014 chasing her 18th Grand Slam title, which would have tied Chris Evert and Martina Navratilova. French player Alizé Cornet spoiled those plans with a gutsy third-round performance.
Cornet had beaten Williams earlier that year and repeated the feat on grass, using her consistent baseline game to frustrate the American. The defeat forced Williams to wait until the US Open to reach that milestone 18th major.
Sabine Lisicki Beats Serena Williams (2013)
German Sabine Lisicki entered her fourth-round match against Serena Williams knowing she faced the defending champion and overwhelming favorite. The 23rd seed played inspired tennis, using her powerful serve and aggressive groundstrokes to dismantle Williams’ game.
Lisicki’s victory ended Williams’ 34-match winning streak and sent her all the way to the final. The German ultimately lost to Marion Bartoli in the championship match.
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John Isner Defeats Novak Djokovic (2022)
American John Isner faced six-time Wimbledon champion Novak Djokovic in the third round, with most expecting a routine victory for the Serbian. Instead, Isner produced one of the finest performances of his career, combining his massive serve with surprising court coverage.
The American’s 6-4, 6-4, 6-2 victory sent shockwaves through the tennis world. Isner proved that on grass courts, anyone can have their day against even the best players.
Tatjana Maria Beats Jelena Ostapenko (2022)
German mother-of-two Tatjana Maria returned to tennis after having her second child and immediately made waves at Wimbledon. She shocked 12th seed Jelena Ostapenko in the second round, using her experience and crafty play style to neutralize the Latvian’s power.
Maria’s composed performance earned her a spot in the later rounds. Her run to the semifinals became one of the tournament’s most heartwarming stories.
Coco Gauff Loses to Dayana Yastremska (2025)
Second-seeded Coco Gauff entered Wimbledon as the fresh French Open champion, but Ukrainian Dayana Yastremska had other plans. The unseeded Ukrainian played aggressive tennis to defeat the American in the first round.
Gauff became just the third woman in the Open era to lose in the first round at Wimbledon immediately after winning Roland Garros. Yastremska’s fearless approach overwhelmed the young American, who struggled to find her rhythm on grass.
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Petra Kvitová Loses to Ekaterina Alexandrova (2021)
Two-time Wimbledon champion Petra Kvitová looked like a serious threat to reclaim her crown when she arrived at the All England Club. Russian Ekaterina Alexandrova had different ideas, using consistent baseline play to neutralize Kvitová’s powerful left-handed game.
The Czech’s strong grass-court record meant nothing against Alexandrova’s determined performance. The upset proved that even former champions face danger in every round at Wimbledon.
Andy Murray Loses to Stefanos Tsitsipas (2018)
Andy Murray’s comeback from hip surgery faced an early test when he drew young Greek Stefanos Tsitsipas in the first round. The former world number one and two-time Wimbledon champion couldn’t handle Tsitsipas’ aggressive style and fearless approach.
The Greek showed no intimidation despite making his Wimbledon debut, signaling the arrival of a new generation. Murray’s loss highlighted how quickly the game can change, even for established champions.
Dominic Thiem Loses to Sam Querrey (2017)
US Open champion Dominic Thiem entered Wimbledon as the eighth seed, but his clay-court success didn’t translate to grass. American Sam Querrey used his big serve and aggressive approach to overwhelm the Austrian’s baseline game.
The upset highlighted the unique challenges that grass courts present, even for the world’s top players. Querrey’s power game proved perfectly suited for the faster surface.
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Naomi Osaka Loses to Yulia Putintseva (2019)
World number two Naomi Osaka’s first-round exit to Kazakhstan’s Yulia Putintseva stunned everyone watching. The Japanese star had won back-to-back Grand Slams but couldn’t find her rhythm on the grass courts.
Putintseva’s crafty play and ability to change pace caught Osaka completely off guard. The defeat proved that adapting to grass remains one of tennis’ greatest challenges, regardless of ranking or recent success.
Simona Halep Loses to Amanda Anisimova (2021)
Former world number one Simona Halep arrived at Wimbledon with high expectations after reaching the 2019 final. Young American Amanda Anisimova spoiled those plans with powerful hitting that overwhelmed Halep’s typically solid baseline game.
The Romanian’s experience and ranking couldn’t save her from Anisimova’s fearless approach. The upset showed that youth and power can triumph over experience and consistency.
Daniil Medvedev Loses to Jan-Lennard Struff (2021)
World number two Daniil Medvedev’s excellent hard-court form meant nothing when he faced German Jan-Lennard Struff on grass. The Russian’s struggles on the surface were exposed by Struff’s aggressive style and powerful groundstrokes.
Medvedev’s defeat reinforced the notion that grass courts remain the great equalizer in tennis. Rankings and recent results often matter less on this unique surface.
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When Grass Courts Level the Playing Field
These upsets prove that Wimbledon’s grass courts don’t care about rankings, reputations, or recent results. The surface demands a specific skill set, and players who adapt quickly often find success against more accomplished opponents.
From defending champions falling in the first round to wildcards winning the entire tournament, these moments show why Wimbledon remains tennis’ most unpredictable major. The magic happens when preparation meets opportunity, and sometimes the underdog seizes the moment perfectly.
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