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

By Charles Perrin Mar 14th, 2024 7:22 AM EDT

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

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

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

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

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

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About the Author

Charles Perrin

More About Charles

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.

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