Wimbledon has always been built around history and tradition, but some of its most memorable days have come when the draw suddenly stops making sense.
Grass can, and it will do that; the unforgiving surface rewards brave serving and quick reactions, which means a favourite can be dragged into the trenches before they have had a chance to settle into the match properly. Once an underdog starts nailing their first serves and taking the ball early, even the greatest champions can look uncomfortable.
That is why Wimbledon has produced some of the most famous moments and shocks the sport has seen. Some were caused by a player catching fire for one afternoon, while others came when a defending champion ran into the worst possible opponent at the worst possible time. For fans following betting in Ireland, these unpredictable results also highlight just how quickly expectations can be overturned on grass.
Lukas Rosol Beats Rafael Nadal, 2012
Rafael Nadal arrived at Wimbledon in 2012 as a two-time champion and fresh from yet another French Open title, which made his second-round defeat to Lukas Rosol feel almost impossible at the time.
Rosol stepped onto Centre Court ranked 100 in the world, but for one day he played with the freedom of someone who had nothing to lose. His hitting was huge, his serving became more dangerous as the match went on, and Nadal could never take control and drag him into the kind of physical contest he usually controlled.
The ending is what made the upset feel so surreal, while the game halted waiting for the roof to close, Rosol went back into the changing room and emerged for the final set looking calm and composed. He served with ridiculous confidence and closed the match out 6-4 in the decider.
It was not only a bad day for the Spaniard, who everyone thought would book his place in the third round. It was one of those results that reminded everyone how quickly grass can turn a match if the underdog keeps swinging.
Sergiy Stakhovsky Beats Roger Federer, 2013
A year later, Wimbledon produced another shock that felt just as hard to process for everyone in attendance and those watching around the world.
Roger Federer was the defending champion in 2013 and had built a reputation at the All-England Club that made it seem almost implausible that he would face an early exit. Sergiy Stakhovsky, ranked 116, did not simply beat him by grinding through long rallies and playing to his strengths; he rushed him.
Stakhovsky used serve-and-volley tennis to his advantage, showing the Swiss legend no respect and constantly moving forward and refusing to let Federer settle into the rhythm that had carried him through so many Wimbledon matches.
The defeat ended Federer’s run of 36 consecutive Grand Slam quarter-finals, which says everything about the magnitude of the result. It was not just that he lost early. It was that one of the most reliable records in modern tennis ended in that second round.
For Stakhovsky, it became the most notable win of his life and the high point of his playing career. For Wimbledon, it was another reminder that even the most comfortable champions can be unsettled on grass.
George Bastl Beats Pete Sampras, 2002
By 2002, Sampras was no longer quite at his peak, but he was still a seven-time champion whose reputation preceded him. That history made his second-round defeat to George Bastl one of the most jarring results Wimbledon has ever seen.
Bastl was ranked 145 and had entered the draw as a lucky loser, which made everyone in attendance believe the match should have been a formality. Instead, on Court Two, which has long been known as the graveyard of champions, he pushed Sampras into a contest that became more awkward with every game he won.
Sampras fought back from two sets down, but Bastl held himself together in the fifth set and won 6-4. Court Two’s reputation became even more significant because it was Sampras’ final appearance at Wimbledon.
Sam Querrey Beats Novak Djokovic, 2016
Novak Djokovic arrived at Wimbledon in 2016 holding all four Grand Slam titles, which made his third-round loss to Sam Querrey feel like someone had made a mistake while writing the script.
Djokovic had won Wimbledon consecutively in 2014 and 2015, and he seemed to have the men’s game under complete control. Querrey was dangerous, especially with his serve, but there is a huge difference between being dangerous and beating Djokovic at a Grand Slam.
For much of the match, Querrey played as though he believed the upset was genuinely possible. His first serve kept him out of trouble, and Djokovic never seemed comfortable whenever he fell behind.
The American eventually won in four sets, ending Djokovic’s long winning run at the majors and opening up the tournament in a way nobody would have expected.
It was a classic Wimbledon shock because it came from a player using one major weapon brilliantly. On grass, that can sometimes be enough to make even the best player in the world become overwhelmed.
Ivo Karlovic Beats Lleyton Hewitt, 2003
Defending champions are meant to ease into Wimbledon, aren’t they, but Lleyton Hewitt’s 2003 campaign ended almost before it began.
Hewitt faced Ivo Karlovic in the first round, and the Croatian qualifier was ranked 203 at the time. On paper, it looked like the reigning champion wouldn’t need to get out of second gear. On grass, Karlovic’s serve changed everything.
Hewitt started well and took the first set, but Karlovic began to grow into the contest and made the match feel deeply uncomfortable for the Aussie. His serving power and his height made normal returning patterns incredibly difficult, while Hewitt found himself under pressure in ways he could not easily solve.
Karlovic won in four sets, making history as the first time in the open era the men’s defending champion would lose in the opening round at Wimbledon.
It was shocking because it happened so early, but it also made perfect sense once the match unfolded. Karlovic had the kind of weapon that could turn a first-round match into a banana skin, especially on grass.
The Grass Always Leaves a Door Open
These results still stand out because there really are no certainties when it comes to Wimbledon. Each favourite on this list arrived with a reputation and expectation, but each ran into an opponent who found the right level at the right time. That is what makes the tournament so dangerous.
Grass is very unforgiving; it doesn’t give players long to figure out problems, a loose service game can decide a set, and a confident underdog can grow taller with every point or advantage they gain. That is why Wimbledon shocks always live long in the memory. They are not just defeats for famous players, but reminders that the All-England Club has never been as predictable as its traditions can make it look.
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