The most shocking upsets in tennis Grand Slams

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While there are plenty of big tournaments on the global tennis tour, no events generate attention like the four Grand Slams on the calendar.

Consequently, the biggest names in both the men’s and women’s game look to have everything fully in order before each major – in attempt to etch their name into tennis playing folklore.

Adding to the difficulty of the task for any of the men looking to win a Grand Slam title, is the increase to a best of 5-set match across all four major tournaments, meaning challengers have to sustain a previously unseen level to upset the odds.

However, with 128 players in both the male and female draws, there is plenty of scope for upsets and in years gone by, there have been some incredible turn ups for the books, across all four Grand Slams.

All of the biggest and best tennis betting sites look to be fully locked in for the significant events on the calendar and if a player can cause a huge shock, in the two-way betting market, there is plenty of value to be had.

Here is a look at some of the most shocking and memorable upsets in the history of Grand Slam tennis:

Robin Soderling vs Rafael Nadal – 2009 French Open

When it comes to being synonymous with one Grand Slam, no player can lay a glove on the 15 French Open singles titles Rafael Nadal managed to win during his incredible career.

Quickly coined the ‘King of Clay’, Nadal won his first title at Roland Garros in 2005 at the age of 19 on his tournament debut and his dominance on the ‘dirt’ is unrivalled.

Success seamlessly followed for the Majorcan, who won the title with relative ease in 2006, 2007 and 2008 and more of the same was expected in 2009.

Nadal breezed through to the last 16 in Paris, and nobody was expected to stop him at the top of the draw, as he lined up against 23rd seed Robin Soderling.

What happened next continues to go down in French Open folklore, as Soderling produced some remarkable tennis to overcome Nadal in four sets – becoming the first man to ever beat him at the French Open.

Soderling’s dream run came to an abrupt halt against Roger Federer in the final but his win over Nadal remains one of the biggest shocks in the history of tennis.

Jelena Dokic vs Martina Hingis – 1999 Wimbledon

As is customary at the beginning of a Grand Slam, the defending champion gets their next campaign underway on the main show court.

When it comes to pomp and circumstance, nowhere compares to Wimbledon and Martina Hingis arrived back at SW19 full of confidence, having lifted the women’s singles title less than 12 months before.

In her way stood Jelena Dokic, a teenage qualifier who had been thrashed by Hingis at the same stage at the Australian Open, merely a few months before.

However, Dokic produced some remarkable tennis on Centre Court, winning 6-2, 6-0 to produce one of the biggest shocks in the women’s game at Wimbledon.

Michael Chang vs Ivan Lendl – 1989 French Open

While Michael Chang’s achievements in the game of tennis may be well documented, he will always be defined by his French Open win at the start of his career.

As a teenage prodigy, Chang had produced some decent tennis to crack the top 20 in the world rankings but his path to victory at Roland Garros will always be defined by his triumph over Ivan Lendl.

Top seed and juggernaut Lendl had cruised through his first three matches before the pair met in the fourth round and nothing looked to be changing, as he went two sets to love up in no time.

However, Chang’s variety and guile caused problems for Lendl and quickly, it became apparent that the pair were in for a real scrap.

Eight-time major winner Lendl was of course up for the challenge and by the fifth set, it looked as if he had seen off the brave challenge of the teenager, who began to cramp in the Parisian heat.

However, with underarm serves and outrageous moon ball tactics, Chang managed to secure an incredible win, which he backed up by going on to lift the title at the expense of Stefan Edberg – securing his only career Grand Slam win in the process.

Roberta Vinci vs Serena Williams – 2015 US Open

With 23 Grand Slams to her name, Serena Williams seldom let big title get away but in 2015, she endured a tough loss at the US Open.

Having overcome some decent opposition in the form of Kiki Bertens and her sister, Venus Williams in the first few rounds, Serena looked to be on course for another Grand Slam triumph.

In her way in the semi-finals stood Roberta Vinci, with the diminutive Italian not known for her singles prowess, being very much more of a doubles specialist.

The stage was set for Serena, who tended to always deliver when it mattered most but Vinci produced some incredible tennis, to overcome the all-time great on her home patch.

Vinci’s 3 set win will go down in Grand Slam folklore, but it wasn’t enough, as she lost to compatriot Flavia Pennetta in the final.

George Bastl vs Pete Sampras – 2002 Wimbledon

In the same way that Rafael Nadal’s links with the French Open have transcended tennis, Pete Sampras and Wimbledon was often referred to as the perfect match.

‘Pistol Pete’s’ big serve and volley game worked a treat at SW19, and the American won seven men’s singles titles at Wimbledon between 1993 and 2000.

A ‘changing of the guard’ defeat to Roger Federer in 2001 felt significant but was by no means a shock and in 2002, Sampras was expected to return to his old stomping ground and challenge for the title once more.

In the second round, he faced lucky loser George Bastl, the type of contest Sampras had been supreme in for over a decade – across all of the Grand Slams.

Bastl won the first two sets, only for Sampras to hit back and take it to five but the Swiss underdog clinched a famous win, reaching the third round of a Grand Slam for the only time in his career and consigning Sampras to one of the biggest Grand Slam shocks of all time.

Sam is a passionate journalist, who looks to create engaging content across a range of sports. Dovetailing his career between sports coaching and sports writing, Sam has travelled the world, delivering daily sports content, across a range of sporting publications globally. Working on a freelance basis, Sam produces content on football, tennis, cricket and golf in the UK, Gaelic Football in Ireland, the NBA in America and on the AFL and horse racing in Australia.
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