It’s late June, which means Wimbledon is just around the corner. The fortnight of tennis starts on 1st July as west London welcomes the world’s best in the third Grand Slam of the calendar year.

While the pre-tournament attention is on the big names like Rafael Nadal, Roger Federer, Serena Williams and Naomi Osaka, it is often the shock results that grab the most headlines in a Wimbledon fortnight.

Nothing sticks in the memory quite like a huge shock, particularly at a Grand Slam tennis event. We have compiled a list of seven of Wimbledon’s most remarkable upsets.


MARIA SHARAPOVA vs Serena Williams (2004)

The 2004 final is considered one of the greatest upsets in Wimbledon history as Maria Sharapova became the third-youngest woman to win the tournament, defeating massive favourite and two-time defending champion Serena Williams in straight sets.

Williams has since gone on to win five more Wimbledon titles and become perhaps the greatest female tennis player of all-time. The defeat to a 17-year-old Sharapova, though, remains one of Serena’s most famous matches.

The 23-time Grand Slam champion is the joint 6/1 favourite to win Wimbledon this year in 888’s sports betting.


MICHELLE LARCHER DE BRITO vs Maria Sharapova (2013)

Michelle Larcher de Brito wasn’t given a chance when she was drawn to face Maria Sharapova in the second round in 2013. Sharapova, the 2004 champion, was the third seed, and obviously one of the favourites to win the tournament.

Multiple falls on the grass rattled Sharapova, as the 20-year-old Larcher de Brito built confidence throughout the match. She was ranked 131st in the world, but the Portuguese youngster put in the performance of her life and was a deserving winner.

Sharapova is a contender to win her second Wimbledon in 2019. Find out more in 888sport’s latest tennis news and betting tips.


JENNIFER CAPRIATI vs Martina Navratilova (1991)

Jennifer Capriati was only 15 years old when she beat Martina Navratilova in 1991. As Capriati ascended into the world’s top 10, she stunned the tennis world with a straight sets quarter-final victory over Navratilova.

The victory made Capriati the youngest person to reach the last four at Wimbledon and saw Navratilova’s earliest Wimbledon exit since 1977.

The then reigning champion had appeared in the last nine Wimbledon finals, winning seven of them. Defeat to Capriati brought an end to Navratilova’s Wimbledon dominance – she never won the tournament again despite appearing in the 1994 final.


NICK BROWN vs Goran Ivanisevic (1991)

Nick Brown was ranked 591st in the world when he beat Goran Ivanisevic at Wimbledon in 1991. It was only the second round, and Ivanisevic had been a semi-finalist the year before.

Brown, given a wildcard entry to the tournament, needed just four sets to beat the big-serving Croatian. He had previously quit the game, and was only a couple of years into his comeback when he defeated a true Wimbledon icon 4-6, 6-3, 7-6, 6-3.

At the time, Ivanisevic was ranked 10th in the world – he went on to win the tournament 10 years later and appeared in three other finals.


GEORGE BASTL vs Pete Sampras (2002)

George Bastl was fortunate to get into Wimbledon in 2002, only being allowed to enter the tournament because of an injury. He beat Denis Golovanov in the first round, setting up a second round clash with Pete Sampras – who was a seven-time Wimbledon champion.

Sampras’ dominance at Wimbledon had been broken by Roger Federer in the fourth round in 2001, but he entered the 2002 edition as the sixth seed and one of the favourites to lift the trophy.

Bastl was ranked 145th in the world at the time of the match; he never won another Grand Slam match.


LUKAS ROSOL vs Rafael Nadal (2012)

Rafael Nadal was a finalist at the Australian Open in 2012 and won the French Open. He had beaten Novak Djokovic three times before Wimbledon came around and looked set for a deep run into the tournament, and perhaps a third title in west London.

Lukas Rosol had other ideas. Making his tournament debut and ranked 100th in the world, it would be an understatement to call Rosol an outsider.

This had all the makings of a walk over for Nadal, who had appeared in four of the previous five Wimbledon finals. Rosol hadn’t made it through Wimbledon qualifying in five previous attempts, but miraculously defeated Nadal in a five-set epic.

Looking to back Nadal to finally win his third Wimbledon title? Find all the information in our Wimbledon 2019 guide.


IVO KARLOVIC vs Lleyton Hewitt (2003)

Lleyton Hewitt was reigning Wimbledon champion in 2003 and the overwhelming favourite in his first-round match against the 6’10”, big serving Ivo Karlovic. Karlovic was playing his first match in the main draw of a Grand Slam, and the nerves showed, as he lost the first set 1-6.

From there, though, he played one of the matches of his life, cruising through the next three sets as Hewitt became the first Wimbledon champion to lose in the first round in the Open Era.

Ranked 203rd in the world at the time, having won just two tour matches in his career previously, this upset was guaranteed to appear on this list.

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About the Author
Sam Cox

Sam is a sports tipster, specialising in the Premier League and Champions League.

He covers most sports, including cricket and Formula One. Sam particularly enjoys those on the other side of the Atlantic Ocean – notably MLB and NBA.

Watching, writing and talking about sports betting takes up most of his time, whether that is for a day out at T20 Finals Day or a long night of basketball.

Having been writing for several years, Sam has been working with 888Sport since 2016, contributing multiple articles per week to the blog.