Greatest Upsets in Tennis Grand Slam History

Wimbledon 4th Round 2001: Roger Federer d Pete Sampras (7-6, 5-7, 6-4, 6-7, 7-5)

A great starting point! Roger Federer, who was the young pretender or apprentice at the time, was taking on one of the greatest grass-court players in Pete Sampras.

The American had made Wimbledon his domain, and before facing the Swiss maestro, he had won 31 matches on the trot at SW19. 

Yes, Sampras was an imposing figure with his big serve and volley game as well as outrageous smashes. But Federer went about trying to unpick the seven-time Wimbledon champion’s game.

This was a match that ebbed and flowed, and Federer dropped to his knees after slashing a backhand that struck the net chord before looping down the line. It was the earliest exit for Sampras on his 10th appearance at Wimbledon.

Sampras ended up retiring in 2003, whereas Federer, well, the rest is history as they say!

Wimbledon 2nd Round 2015: Dustin Brown d Rafael Nadal (7-5, 3-6, 6-4, 6-4)

Rafael Nadal was loved during his career, but he wound up with just two Wimbledon titles which would indicate grass wasn’t his favoured surface.

Nevertheless, few would have expected a shock when unheralded German Dustin Brown rocked up on Centre Court. Ranked 102 in the world, Brown brought his A-game to the table as Nadal folded.

Brown even had to come through three rounds of qualifying to book his spot in the main draw, but it was an unforgettable day for him. 

Nadal’s forehand broke down and the errors flew off his racquet. But Brown wrapped things up in style, serving an ace. However, after his monumental effort against Nadal, Brown exited in the following round against Viktor Troicki, losing in four sets.

French Open Quarter-Final 2018: Marco Cecchinato d Novak Djokovic (6-3, 7-6, 1-6, 7-6)

Novak Djokovic is arguably the greatest men’s player to have graced the game. With 24 titles and counting to his name, there are few things he hasn’t achieved.

Indeed, he’s a three-time winner at Roland Garros, but the red dirt was in an unforgiving mood in 2018 against the Italian Marco Cecchinato in the quarter-finals.

Cecchinato, who was ranked 72nd in the world, had never won a main-draw match at a Grand Slam before his stunning run in Paris. However, Djokovic, who had a neck injury during the first set, looked distinctly off-colour, and Cecchinato pounced.

It was a career-defining win for Cecchinato, who had previously served an 18-month ban for match fixing.