Top 10 Biggest Grand Slam Upsets in Men's Tennis Since 2000

Tennis has given us some great matches through their four Grand Slam tournaments: the Australian Open, Roland Garros, Wimbledon, and the U.S. Open. In all of these tournaments, we’ve seen the cream of the tennis crop go head to head against each other in some of the most thrilling match-ups possible in this sport. However, what’s possibly even more exciting than that is seeing the giants of tennis be swept up from under their feet by unheralded underdogs, shocking the tennis world in the process.

Some of these victories are ones that put certain players on the map briefly, while others were important victories that paved the way for eventual victories at those Grand Slam tournaments. In some cases, these players were placed outside the top 100 in the men’s tennis rankings, but ended up winning matches against the sport’s elite. Even if their luck runs out shortly after their famous victory, those victories are still memories those players can cherish for the rest of their careers and their lives.

For others, such as Rafael Nadal in 2005 and Novak Djokovic in 2008, they were upset victories that caused them to eventually become among the best players the sport gets to witness right now. In the case of Nadal, his victory in 2005 against Roger Federer at the French Open led him to being the one who challengers have to upset in subsequent years – just ask Lukas Rosol, Stanislas Wawrinka and Robin Soderling.

In any case, these matches have given us some of the most exciting men’s tennis we’ve seen in recent years, and they have shown us that no tennis match is ever played on paper – even if the odds are overwhelmingly in the favour of tennis’ heavyweights. Here are the top 10 Grand Slam matches since 2000 with the biggest upsets.

10 Rosol beats Nadal at Wimbledon in 2012

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A relative newcomer to the tennis world in 2012, Czech player Lukas Rosol turned heads in a big way by beating Rafael Nadal in the second round at Wimbledon – which Nadal had won twice. Nadal was off to a good start by winning the first set, but Rosol’s resiliency paid off, with the Czech winning the match in five sets (6-7, 6-4, 6-4, 2-6, 6-4). However, Rosol’s luck would soon run out: he lost in the third round to German player Philipp Kohlschreiber that year, and a third round appearance remains Rosol’s biggest accomplishment at Wimbledon.

9 Stakhovsky beats Federer at Wimbledon in 2013

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Ukrainian player Sergiy Stakhovsky had the odds well stacked against him in 2013 when faced with the unenviable task of taking on Roger Federer at Wimbledon. For Stakhovsky, it would prove to be well worth it: he would beat Federer in four sets (6-7, 7-6, 7-5, 7-6) in the second round of the tournament. Stakhovsky couldn’t carry his huge victory into the third round, however, and lost to Jurgen Melzer in four sets. For Federer, the loss meant that he was unable to defend his Wimbledon title from the year before, after having won it seven times already.

8 Djokovic beats Federer at the Australian Open in 2008

In 2008, Novak Djokovic was climbing into the Top 10 of the men’s tennis rankings, but had yet to truly establish himself as one of the sport’s current greats. At that year’s Australian Open, he would take one giant step towards changing that: he defeated the three-time winner/defending champion Roger Federer in straight sets (7-5, 6-3, 7-6) to advance to the final, where he beat Jo-Wilfried Tsonga to win his first ever Grand Slam title. With the victory, Djokovic disrupted the Federer/Nadal monopoly on the men’s Grand Slam singles events for the first time since the 2005 Australian Open.

7 Nadal beats Federer at Roland Garros in 2005

Before becoming the elite player we know him for being today, Rafael Nadal was an up-and-coming teenager in the tennis world in 2005 after being ranked only 51st in the world by the end of 2004. During the French Open, Nadal would truly start to break out: on his 19th birthday, Nadal would upset Roger Federer – the same player who beat him in the fourth round of that year’s Australian Open – in the semi-finals on his path towards eventually winning the tournament that year. It would be Nadal’s first Grand Slam, and one of many chapters in one of the biggest rivalries in tennis.

6 Johansson beats Safin at the Australian Open in 2002

Prior to the 2002 Australian Open, the highest Grand Slam finish for Swedish player Thomas Johansson was twice reaching the quarterfinals at the U.S. Open both in 1998 and 2000. However, Johansson brought his best performance in a Grand Slam tournament in 2002, beating Russian heavyweight Marat Safin in a four-set match (3-6, 6-4, 6-4, 7-6) in the final. In large part because of his victory at the open, Johansson would get to a career-high ranking of seventh overall in May 2002. He would win a silver at the 2008 Olympics in men’s doubles before retiring from tennis the following year.

5 Wawrinka beats Djokovic and Nadal at the Australian Open in 2014

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A trip to the U.S. Open semifinals the year before was impressive in and of itself, but Stanislas Wawrinka would easily top that at the Australian Open the following year. Upon reaching the quarter-finals, the Swiss player would be facing four-time defending champion Novak Djokovic. To the surprise of many, Wawrinka won in five sets (2-6, 6-4, 6-2, 3-6, 9-7) to send Djokovic crashing out. A semifinal win against Tomas Berdych would bring Wawrinka to the final against Rafael Nadal, who would suffer a back injury during the match. The four-set victory for Wawrinka would give him his first ever Grand Slam.

4 George Bastl beats Pete Sampras at Wimbledon in 2002

With Swiss player George Bastl ranked 145th in the world, people weren’t wondering whether or not Pete Sampras would beat him, but by how many sets the seven-time world champion would beat him. However, the upstart Bastl would upset Sampras in a five set match (6-3, 6-2, 4-6, 3-6, 6-4) after the Swiss player qualified for that year’s Wimbledon tournament only because another player pulled out through injury. Bastl would lose in the third round to David Nalbandian, and the win against Sampras would remain his biggest tennis achievement, only peaking at number 71 in the men’s singles rankings in 2000.

3 Robin Soderling beats Rafael Nadal at Roland Garros in 2009

Swedish tennis star Robin Soderling had been steadily rising into the top 20 of the world men’s tennis rankings by the time 2009 came around, but no one expected him to topple Rafael Nadal at the French Open – a tournament Nadal had won four straight times and of which he was in the middle of defending his title. But when the fourth round came along, Soderling upset Nadal in a decisive four-set victory (6-2, 6-7, 6-4, 76), snapping Nadal’s 31-match streak at the tournament. Soderling would go on to reach the final – only to lose to Roger Federer – and remains the only player to beat Nadal at Roland Garros.

2 Del Potro beats Federer and Nadal at the U.S. Open in 2009

If Soderling beating Nadal in 2009 at the French Open was an impressive feat by itself, Juan Martin del Potro would manage something even more impressive at the U.S. Open that same year. Upon reaching the semi-finals, the Argentine would defeat Rafael Nadal convincingly  in straight sets (6-2, 6-2, 6-2). He would then face the top-ranked male tennis player in the world, Roger Federer, in the final. Del Potro ended up beating the five-time U.S. Open champion in five sets (3-6, 7-6, 4-6, 7-6, 6-2) in a come from behind victory – his first victory against Federer in six match-ups.

1 Goran Ivanisevic wins Wimbledon in 2001

Sitting at 125th in the world rankings, Goran Ivanisevic was hardly expected to make much noise at Wimbledon after getting in to the tournament as a wildcard player. However, he defied odds and flipped expectations onto their heads: beating Carlos Moya, Andy Roddick, and Marat Safin to then beat Tim Henman in his own country in the semi-final. Then came the final match against Patrick Rafter, who Ivanisevic beat in five sets (6–3, 3–6, 6–3, 2–6, 9–7) to become the first ever wildcard to win it all at Wimbledon. Ivanisevic would retire briefly the following year due to shoulder surgery, but would occasionally come back in subsequent years. However, he’d never top his accomplishment at Wimbledon.

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