Wimbledon's biggest ever upsets: 8 shocking tennis matches that no-one could have predicted

The 138th Wimbledon Championships will toss up its first serve on Monday, commencing two weeks of high-level tennis at the sport’s most storied and prestigious venue.

For the home crowd, this will be the first Wimbledon following Andy Murray’s retirement. It’s not completely outside of the realms of possibility for a British champion to emerge – Jack Draper has had an excellent year, leaving him fourth in the world rankings, while Emma Raducanu will always have that 2021 fourth round run and subsequent US Open victory to offer a glimpse of hope.

Still, there’s no escaping the fact that in order for a Brit to win another Wimbledon tournament this year, it’s going to take several shock results.

Thankfully, while the cream usually rises to the top in this most unforgiving of sports, upsets do happen. We’ve assembled eight of the biggest and most memorable below.

These were results that, on paper, simply shouldn’t have happened. Each of these saw great champions in prime condition (at least on paper), coming up against players ranked way below them.

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1. Lukas Rosol vs Rafael Nadal (2012)

We’ll start out with this one because it emerged after the match that Rafael Nadal was really struggling with his knees at the time. Those mitigating circumstances shouldn’t detract too much from Lukas Rosol’s second round victory, however.

After all, this was a player who would peak at a worldwide ranking of 37 some two years later, coming up against one of the greatest ever players to ever pick up a raquet. This was Nadal in his prime too – dodgy knees notwithstanding – and just two years out from his second Wimbledon title win.

2. Alize Cornet vs Serena Williams (2014)

Williams had already experienced a shock exit two years prior (see elsewhere on this list), but that didn’t make her 2014 exit any less of a shock. She was still very much at the top of the women’s game, and would go on to win the US Open soon after, as well as the next two Wimbledon singles tournaments.

However, here in 2014, France’s Alize Cornet had all the answers. She beat Williams for the second time that year after losing the first set 1-6.

3. Ivo Karlovic vs Lleyton Hewitt (2003)

Hewitt might have done his best work in the brief period between the reigns of Pete Sampras and Roger Federer, but his high energy game had won him the US Open in 2001 followed by Wimbledon 2002. There was a world number one ranking sandwiched in between.

That’s why it was such a shock when Hewitt tumbled out of Wimbledon 2003 at the third round stage. The big-serving (and just plain big) Ivo Karlovic could be a handful for anyone on his day, but this was the first time a defending men’s champion had ever gone out in his first game.

4. George Bastl vs Pete Sampras (2002)

We’ve just emerged from arguably the greatest ever period of men’s tennis, with three all-timers (and Andy Murray) all competing at the very highest level. Let’s not forget the preceding generation, however, which saw the majestic Pete Sampras all but perfecting the classic serve-and-volley style.

In 2002, the American was surprisingly ejected from a tournament he had dominated until relatively recently. While it’s true that this was Sampras’s final year, the seven-time champ was still expected to sweep away the challenge of George Bastl – a ‘lucky loser’ who had failed in his qualifying match.

5. Sergiy Stakhovsky vs Roger Federer (2013)

This was a brutal year for the seeded players, but by far the biggest shock came in the second round, when the great Roger Federer went crashing out. At that point, Ukraine’s Sergiy Stakhovsky had never even beaten a top 10 player, let alone the greatest to ever play the sport.

We weren’t talking about a Federer on the wane, either. The Swiss legend was at the peak of his powers, just 30 years of age and already a seven time Wimbledon champion – the last of which had arrived just the year before.

6. Sabine Lisicki vs Serena Williams (2012)

We’re not sure what was in the Robinsons during the 2012 tournament, but following Rafael Nadal’s shock second round exit it was the turn of the greatest player the women’s game has ever seen to be sent packing. In Sabine Lisicki’s defence, she’s no chump, and she would rise to a career high of number 12 in world this very year.

Still, it was a relatively inexperienced version of the German who took to the court against the dominant champ. In a tightly fought match, Lisicki responded to a 1-6 loss in the second set to win two sets to one.

7. Peter Doohan vs Boris Becker (1987)

As the 1987 tournament rolled around, Boris Becker had won the two previous men’s singles titles, and he hadn’t even yet hit 20. It would have taken a brave person to bet against him.

That brave person would have been significantly richer by the end of the first week, however, as the German prodigy crashed out in the second round to Peter Doohan, then ranked a mere number 70 in the world. Becker would recover to contest the 1988 final and win the 1989 tournament, but Doohan will forever be known as “The Becker Wrecker” back in his native Australia.

8. Lori McNeil vs Steffi Graf (1994)

In the years immediately preceding Serena Williams, it was Germany’s Steffi Graf who dominated women’s tennis. Throughout her career in the late ‘80s and ‘90s, Graf won every major tournament at least four times, and even Williams herself was unable to beat her total of seven Wimbledon titles.

So it was a bit of a shock, to put it mildly, when America’s Lori McNeil beat the reigning champion in the first round of the 1994 tournament. McNeil was no mug, having reached the semi-final in 1987, but that was seven years prior, while Graf was still very much at the top of her game.

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