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Wimbledon: Five biggest men’s shocks

The 2023 Wimbledon men's singles events sparks into action on Monday 3rd July and there are a number of up-and-coming talents with the credentials to cause a stir by springing a surprise on the seeded stars.

Novak Djokovic has won Wimbledon on each of the last four occasions and the super Serb is 8/13 to maintain his dominance and move level with Swiss great Roger Federer with eight titles at the All England Club. 

World number one Carlos Alcaraz is 10/3 to claim his first grass-court major with Russia's Daniil Medvevev 16/1 and impressive Italian Jannik Sinner an 18/1 chance. 

The class tends to rise to the top at Wimbledon but there have been plenty of upsets down the years and with nobody safe from an early elimination at SW19, we have selected five of the biggest upsets during the Open era.

What2023 Wimbledon Men
WhereAll England Club, Wimbledon, London
WhenMonday 3rlyd Ju to Sunday 16th July 2022
How to WatchBBC or bet365 Live Stream
OddsNovak Djokovic 8/13, Carlos Alcaraz 10/3, Daniil Medvedev 16/1, Jannik Sinner 18/1

Peter Doohan v Boris Becker (1987)

Despite being just 19, Boris Becker headed to Wimbledon in 1987 as the world number one and bidding to record a hat-trick of grass-court Major wins.

Few would have anticipated the rising German star to slip-up in his second-round contest with unseeded Australian player Peter Doohan, the world number 70 who went on to win just one title on the ATP Tour.

But that is how events proceeded, with Doohan producing arguably a career-best to prevail in four sets, and it was a moment never to be forgotten in the Aussie's career.

That headline victory earned Doohan the nickname 'The Becker Wrecker', although his tournament came to an end in the fourth round when he was beaten by Slobodan Zivojinovic.

Becker bounced back to finish runner-up in 1988, before going one better a year later when exacting his revenge on talented Swede Stefan Edberg in the final.

Goran Ivanisevic v Pat Rafter (2001)

If at first you don't succeed, try, try again is a mantra Goran Ivanisevic has lived by and after three narrow misses, the Croatian upset the odds to finally get his day in the Wimbledon sun.

On three occasions - in 1992, 1994 and 1998 - Ivanisevic finished runner-up at Wimbledon and by 2001 his time at the top looked limited.

However, the Croatian would become the lowest-ranked player and only wildcard to win Wimbledon, in the process rewarding his most loyal supporters at triple-figure odds.

Ivanisevic recorded wins over Carlos Moya, Andy Roddick, Greg Rusedski and Tim Henman before beating Pat Rafter in an epic five-set final, prevailing 9-7 in a nervy decider.

Ivo Karlovic v Lleyton Hewitt (2003)

Lleyton Hewitt became the first men's defending champion in the Open era to lose in the first round when he bumped into Croatian giant Ivo Karlovic.

Hewitt had outclassed David Nalbandian 6-1 6-3 6-2 in the Wimbledon final 12 months earlier, and the Australian top seed looked to be in decent shape when taking the opening set of his title defence 6-1.

However, the 6ft 11in qualifier had other ideas and his serve was a constant problem for Hewitt, who was eventually beaten 1-6 7-6 6-3 6-4.

Few were aware of the talents the towering Karlovic possessed but the big-serving Croatian then also went on to make the quarter-final at Wimbledon in 2009.

Hewitt failed to build on his 2002 title triumph and made only one semi-final appearance from his subsequent 13 visits to SW19.

Rafael Nadal v Lukas Rosol (2012)

In 2012, two-time Wimbledon champion Rafael Nadal suffered a shock second-round defeat to world number 100 Lukas Rosol in a five-set thriller.

The Spaniard had reigned supreme at the All England Club in 2008 and 2010 but had no answer to Rosol, who was making his main draw debut at Wimbledon after losing in the first round of qualifying for the previous five years.

Nadal headed to Wimbledon in confident spirits, having just recently claimed his seventh French Open title, and looked like he was going to survive an almighty scare when levelling the match at two sets apiece.

However, with play then suspended while the roof was closed before the deciding set, it was Rosol who settled best to record a landmark success.

It also became the first time that Nadal had lost before the third round of a Grand Slam since he lost to Gilles Mueller in the second round at Wimbledon in 2005.

Ten years on and Nadal is still at the top dominating and, having won the opening two Grand Slam events of the season in Australia and France, is again considered a leading contender this year.

Roger Federer v Sergiy Stakhovsky (2013)

Although considered the greatest grass-court player of all-time, Roger Federer showed that nobody was invincible and his second-round defeat to Sergiy Stakhovsky in 2013 remains one of the biggest upsets ever.

By this point, Federer, who was also the defending champion, had seven Wimbledon wins to his name and needed one more to surpass the achievements of Pete Sampras.

Many had hoped the Swiss star could record that feat this year but on a day subsequently labelled Wacky Wednesday, because the seeds were dropping like flies, he had to play second fiddle to the Ukrainian world number 116.

It was the first time in 36 Grand Slam events that Federer has not reached at least the quarter-final, although he did eventually move one Wimbledon win clear of Sampras when defeating Marin Cilic in the 2017 final.

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