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Six of the Greatest Ever Upsets in Men’s Tennis History

Charles Perrin for Bookies.com

Charles Perrin  | 6 mins

Six of the Greatest Ever Upsets in Men’s Tennis History

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Tennis fans have been blessed over the years as they have borne witness to some iconic moments as well as being treated to sustained brilliance in the Grand Slams from the game's elite.

There have been many rivalries that have dominated the upper echelons of men's tennis and that encompasses Bjorn Borg and John McEnroe through to Pete Sampras and Andre Agassi and Roger Federer and Rafael Nadal.

The traditional 'Big Three' consisting of Federer, Nadal and Novak Djokovic have taken the game to new heights and they have all enjoyed trophy-laden careers. However, there have also been some matches in years gone by that have sent shockwaves through the sport.

While the current season has been put on hold due to the coronavirus outbreak, Bookies.co.uk revisits six of the greatest tennis upsets.

  1. Roger Federer vs Pete Sampras (Wimbledon fourth round, 2001)

  2. This was the king versus the pretender. Sampras had dominated on the hallowed turf of SW19, claiming seven of his 14 Slam titles there. Federer was a precocious talent, but he broke down the American in five thrilling sets - 7-6, 5-7, 6-4, 6-7, 7-5.

    Federer slumped to his knees after slapping a forehand down the line to seal the match, it felt that it was an end of an era for Sampras. Who would have known at that point that Federer would dominate men's tennis in the fashion he did? But the rest is history, as they say.

  3. Thanasi Kokkinakis vs Roger Federer (Miami Open second round, 2018)

  4. Little was known about Thanasi Kokkinakis until he met his idol Federer. The Greek was competing in just his fifth tournament over seven months at the time after being ravaged by injuries, but he stunned the patrons with an exhilarating display.

    After recovering from going a set down, Kokkinakis prevailed in three epic sets - 3-6, 6-3, 7-6 (4). Federer was world No. 1 at the time and it was just the second occasion in 18 years that he had been defeated by a player ranked as low as Kokkinakis (175).

  5. Novak Djokovic vs Marco Cecchinato (French Open quarter-finals, 2018)

  6. Djokovic had been going through a period of introspection at this point. And he was put to the sword by the relatively unheralded Marco Cecchinato. The Italian - who up until that point - had never won a match at a Grand Slam event let alone Roland Garros, charged into the last four on the red dirt in Paris.

    The world No. 72 raced into a two sets to love lead and although Djokovic grabbed the third set and led 5-2 in the fourth, it wasn't meant to be for the Serb who required treatment on a shoulder problem during the match. Cecchinato belied his world ranking and produced some extraordinary tennis. He may have required four match points, but he wrapped up the match in style when his backhand passing shot dipped on the line to knock out the 2016 champion.

    Djokovic was rather salty in his post-match press conference and was strange was that he wanted to speak to press immediately after coming off court. He described the defeat as a 'hard one to swallow'. His conduct was bizarre and it was clear how much the defeat affected him. While 2018 was something of an annus horribilis for Djokovic, he managed to overcome his problems and his rise back to the top of the men's game has been nothing short of sensational.

  7. Novak Djokovic vs Hyeon Chung (Australian Open fourth round, 2018)

  8. Djokovic is no stranger to an upset and he was on the receiving end of another upset, this time by Hyeon Chung. Melbourne has been a happy hunting ground for the Serbian, but he was below par for his sublime standards and he was made to pay the price. He had no answer for Chung who was a straight-sets winner - 7-6 (7-4) 7-5 7-6 (7-3). Djokovic required treatment on his shoulder after the first set and he was in considerable pain.

    Djokovic tried to rally the crowd, but he must have felt like he was playing against himself in the mirror as Chung had him on the rack and making him chase down every ball. It was Chung's biggest win as he closed out the match having spent three hours and 21 minutes on the court. Chung broke into the world's top 20 in 2018, but little has been heard about him since.

  9. Dustin Brown vs Rafael Nadal (Wimbledon second round, 2015)

  10. For all the success Nadal has had in his career, he has found things harder to come by at Wimbledon. The mercurial Spaniard - a two-time champion at SW19 - was stunned by little known Dustin Brown in the second round. Brown played out of his skin from start to finish and dropped one set en route to victory.

    The German, who was then ranked 102 in the world, had only reached the third round of a Grand Slam for the third time. Brown wrapped up the match in style with an ace. After toppling Nadal, his chances of reaching the second week of the tournament were ended by Viktor Troiki.

  11. Michael Chang vs Stefan Edberg (French Open final, 1989)

  12. This match will live long in the memory and it was a crowning moment for Michael Chang. The American was only playing his fifth Grand Slam event and after showing incredible determination to knock out world No 1 Ivan Lendl in the fourth round, he was inspired once more against Stefan Edberg.

    Chang was the pioneer of underarm serving that nowadays is frequently used by Nick Kyrgios. But Chang was also a gifted athlete and he mounted a stirring comeback against Edberg in the final, fighting back from two sets to one down to prevail 6-1, 3-6, 4-6, 6-4, 6-2. In the process, Chang - who was only 17 years old - became the youngest men's Grand Slam champion. It was to be his only Major title during a 16-year career.

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About the Author

Charles Perrin for Bookies.com
Charles Perrin
Former overnight online sports editor for the Daily Express, Charles is an experienced writer with a background in sports betting, particularly tennis, cricket and soccer.