From all-teenage finals to unknown wildcards firing past tennis’ undisputed legends, the Grand Slams have spoilt us with wildly unpredictable turns and turnouts over the years. Everyone loves an underdog, even when – or perhaps especially when – they’re up against the biggest names in the game.

Here, we’ve listed what we consider to be the greatest upsets in tennis history. With Wimbledon just around the corner, we hope we may have to make some edits soon…

10. Andy Murray vs Mischa Zverev, Australian Open 2017

Ranked no.1 in the world heading into the 2017 tournament, many Brits felt it was finally Murray’s time to take the crown, the clear favourite. His fourth round tie against world number 50 Mischa Zverev was viewed as nothing more than a necessary step to the quarter-finals, hardly a cause for concern, but when the German snatched the first set 7-5, uncertainty started to creep into the Rod Laver Arena, and it went from bad to worse for the tournament’s blistering favourite.

After salvaging the second set 5-7, Murray succumbed to a 6-2, 6-4 annihilation as Zverev’s old school serve and unforgiving volleys smashed the Scot’s chances to secure another grand slam to his name – and he failed to win another after Wimbledon 2016.

9. Serena Williams vs Roberta Vinci, U.S. Open 2015

Serena Williams is synonymous with tennis. Chasing her first ever Calendar Slam, a feat which only five players have ever accomplished, the stage was set for the US star to cement her place as one of the true legends of the game.

Facing Italian veteran Roberta Vinci, who was placed at an 18/1 win by the bookies, the match began as the world predicted – the first set fell straight into the palms of a fearless, indestructible looking Serena. The Flushing Meadows knew what to expect next – they’d been here enough times before.

But, in one of the most dramatic shifts of momentum the sport has seen, Vinci stunned Flushing Meadows with a faultless performance, soaring into the final 2-6, 6-4, 6-4.

8. George Bastl vs Pete Sampras, Wimbledon 2002

Seven-time champion Pete Sampras may have passed his peak by Wimbledon 2002, but he was still the overwhelming favourite for the second round tie against lucky loser George Bastl – and for the whole tournament, for that matter.

When the 145th ranked Swiss won the first two sets in a blistering start, Centre Court started to twitch, starting to believe for the first time that they may be about to witness something remarkable. But when Sampras, the champion he is, responded by storming his way to the following two sets, there only seemed one winner in the fifth and final act.

Bastl did not cave – he showed his nerve, and relentless determination, when he battled his way to the final set, 6-4, in one of the greatest games, and no doubt the greatest upset, of his career.

7. Cori Gauff vs Venus Williams, Wimbledon 2019

When 15-year-old wildcard Cori Gauff, known as Coco, drew her lifelong hero Venus Williams in the first round of Wimbledon three years ago, it was painted as tennis’ star of the future colliding with one of its brightest stars of the past and present.

But a ferocious performance by the teenager, in her first ever grand slam match, twisted the timings on this fateful day in London. Soaring her way to the second round, and to instant global fame, Coco’s 6-4, 6-4 victory over her fellow American, 24 years her senior, shocked the world – no one could deny the emphatic shift it represented in women’s tennis.

Coco went on to reach the fourth round of the tournament, being the youngest player to do so for 28 years.

6. Robin Soderling vs Rafael Nadal, French Open 2009

There’s no doubt about it – Rafael Nadal is the King of Clay. Winning the previous four consecutive titles, he was such astounding favourite for the 2009 French Open that even defeat by Djokovic or Federer would have been deemed a great upset.

So when 23rd seed Robin Soderling killed his 31-game winning streak at Rolland Garros, it’s safe to say no one quite knew how to respond. Nadal, being the gentleman he is, gave complete credit to Soderling and refused to talk about his sub-par performance in fear it would distract from the Swede’s unbelievable triumph.

5. Lorni McNeil vs Steffi Graf, Wimbledon 1994

There was one sign, and one sign only, that unseeded Lorni McNeil could put up a fight against defending champion Steffi Graf – she had beaten the undisputable world number 1, two years prior.

Maybe that’s what gave her the confidence she could do it again, but for whatever reason, the American was on the offensive against her superior from the off, capitalising on an uncharacteristically tame Graf to take the game 7-5, 7-6 (5). That rainy afternoon was Graf’s only loss at Wimbledon between 1991 and 1994.

4. Nick Kyrgios vs Rafael Nadal, Wimbledon 2014

It’s easy to forget that when Kyrgios blew the world Number 1, Rafael Nadal, off Centre Court in the last 16 of Wimbledon, he was an 18-year-old wildcard who no one predicted would pose a challenge to tennis’ all-time great.

But his nerveless performance, which sparked an intense rivalry between the two that still persists today, showed no signs of fearing the omnipotent figure that is Nadal – with booming serves, cheeky tricks and arguably the shot of the tournament, the youngster’s four-set victory was well-deserved, and saw the birth of one of the most talented, if controversial names in tennis.

3. John Millman vs Roger Federer, U.S. Open 2018

Roger Federer had never lost to a player that was outside the Top 50 – but on this blistering day in New York, that record was swiftly demolished. John Millman, ranked 55th in the world, played the tennis of his life to crush the campaign of the five-time champion in four sets, 3-6, 7-5, 7-6 (7), 7-6 (3).

Renowned for being good friends off the court, the Australian’s electric form – with 8 aces and a +22 winners-to-error ratio – proved too much for Federer on the day, whose game failed to ever set into place. That shouldn’t detract from the monumental achievement of the 29-year-old outsider in this epic fourth round clash, widely regarded as the game of his career to date.

2. Emma Raducanu vs Leylah Fernandez, U.S. Open 2021

The clash of the 18-year-olds at Flushing Meadows last year was perhaps the greatest shock of all – that these two, formerly unknown names, had blazed past some of tennis’ all-time greats to land a place in the final – both their first in a grand slam

Heralded as the fight of the future, both teenagers were unwaveringly calm – unlike their parents – and a tense, tight match ended 6-4, 6-4 to the British wildcard, who didn’t drop a single set in three matches of qualifying and seven main draw contests.

Radacanu burst onto the elite world of tennis that day – becoming the first British woman to win a Grand Slam singles title since 1977, as well as the new British no. 1. Her future looks bright – and a re-match between these overachieving youngsters surely awaits us…

1. Richard Krajicek vs Pete Sampras, Wimbledon 1996

Wimbledon in the 1990s belonged to one man and one man only – Pete Sampras. Relinquishing just one title between 1993 and 2000, it came to one of the most unlikely of candidates, overwhelming outsider Richard Krejicek, who defeated the three-time champion in straight sets.

The title had effectively been handed to Sampras before the tournament kicked off, and his unrivalled dominance in the years that followed only added to the testament of this almighty upset. A fairytale ending was indeed in store for the Dutchman, who went on to win his only Grand Slam title that year.