Introduction: Celebrating the rich history of Wimbledon
These days, it's almost impossible to think of tennis without its most prolific championship coming to mind. Wimbledon has played host to international competition since 1900 when May Sutton of the United States won the women’s singles, but it started out as a domestic competition in England where its humble audience of 200 would grow year by year after its beginning in the 1870s.
In this article, we will be taking a look at Wimbledon iconic matches that proved to be both extremely memorable and significant in the history of the sport. We’ll look back at moments that changed the sport itself forever, as well as the career defining matches that gave rise to household names in tennis that are now inextricably linked to the sport in our mind and media.

May Sutton vs Dorothea Chambers (1905)
We mentioned her in the introduction, and now let’s take a closer look at one of the matches early in Wimbledon’s history which helped define it as a platform for showcasing international tennis talent.
May Sutton from the US faced off against Dorothea Chambers of the UK in a final which would crown her as the first international champion of the Wimbledon women’s singles.
It wasn’t just the prestige of the title that made her an icon, May was known for breaking down conventions and challenging stereotypes of the time, which would eventually lead to the women’s game being what it is today.
Departing from the overbearing modesty of the women's standards at the time, Sutton chose to roll up her sleeves, a daring move which shocked at the time, but symbolized her willingness to put everything on the line to win and prove that women could be just as competitive in their brackets as their male colleagues.
The match itself featured May Sutton’s characteristically powerful strokes and potent serves which were previously unseen from other female players. Sutton’s game raised the bar for women’s sport and paved the way for the formidable athletes we know and love today.
Björn Borg vs John McEnroe (1980)
With two polarizing personalities such as these, there was always bound to be an incredible match.
Björn and John certainly delivered upon these expectations and left behind a gruelling exchange of skill and tenacity which is endlessly replayed and analyzed by fans and tennis players alike, hoping to learn as much as they can from the two experts going head-to-head with almost opposite styles of play.
Nicknames
Björn was known as “The Ice Man”, thanks to his ensemble of cool and calm characteristics. His style was one of consistency and low emotion, playing the game as if it were an exact science and relying on his fundamentals to deliver the results he needed, regardless of who he was facing.
McEnroe was the opposite, known to fans and critics alike as “The Fiery American”, whose play, unlike Björn Borg’s, channelled his passion and emotion and allowed him to deliver high pace, unpredictable serves and engage in rapid rallies on his own terms.
When seeing two contrasting styles like this engage, you might expect one to prevail over the other, yet to the surprise of many onlookers, it seemed that both approaches to the game were equally valid.
The most iconic moment from this duel was the fourth set tie-break, which saw McEnroe come back from the brink, defending successfully from five match points, before bringing it back and winning the set 18-16.
This exchange remains in the hearts and minds of many long time fans of the sport as one of the greatest displays of stamina and mental resilience in not just tennis, but sporting history as a whole.
The Result
Despite McEnroe's incredible effort in the fourth set tiebreaker, Borg would go on to show his own expertise by winning the fifth and final set, which would lead him to have earned his fifth consecutive title an achievement which would permanently etch him into the history of tennis as one of the greatest grass players of all time.
After achieving his victory, the contrasting personalities continued to be shown, with a minimal and composed reaction from the winner, Borg, compared with the obvious emotions shown by McEnroe.

Wimbledon is a big event with a lot of history, so its iconic matches is some of the essential information you should know.
Rafael Nadal vs Roger Federer (2008)
They need no introduction, they’re perhaps the biggest names in the sport! Rafael Nadal and Roger Federer’s showdown in the 2008 Wimbledon tournament is often referred to by fans and journalists alike as the greatest tennis match to ever be played.
Just about everything came together to create an atmosphere of never seen before tension and drama, which lived up to the huge expectations leading up to the match.
Buildup
Prior to the match, Federer was absolutely dominant in Wimbledon, sitting on top of a remarkable 65 game win streak and having held onto the title for five consecutive years, (from 2003-2007).
No one could be blamed for expecting him to take home another victory, but many speculators saw potential in the “king of clay” Nadal, who had been building up his grass game to impressive levels, just in time to make things interesting.
The Longest Match in Wimbledon History (at the time)
Spectators of the match received more than they bargained for, the match itself went on for 4 hours and 48 minutes, making it the longest ever Wimbledon match at that time.
Nadal and Federer ended up playing a full five sets in a captivating back and forth; each time one of them took the advantage, the other would take it back, making fans of both players nervous and uncertain of the outcome.
The first two sets went to Nadal, creating the illusion that he might win the whole thing outright, but in the following two sets, Federer went on to display his unequalled composure, contesting nail-biting tie-breakers to even things out and bring the game to its fifth set.
Dramatic Delays
Due to the weather conditions, the match had to be delayed several times, causing tensions to rise and for the end of the match to be played under a darkening sky.
The final set had a dramatic atmosphere that is permanently stuck in the minds of anyone who witnessed it, especially those who had the privilege of seeing it live.
It’s the kind of match that you would assume to be the work of Hollywood fiction, were it not documented on live television.
The Fifth and Final Set
When the fifth set went ahead, it was anyone’s game and it was a long set at that. Both players fiercely held their ground until the 15th game where Nadal was finally able to find a lead 8-7. He used this lead to close out the match 9-7 before collapsing to the floor from his efforts.
The result both shocked and amazed viewers all over the world, who could not have asked for a closer match.
While Federer was understandably disappointed, he remained humble and courteous, offering a heartfelt and respectful runner-up speech, which reflected on his admirable sportsmanship and appreciation for the skill of his opponent.
The triumphant Nadal ran to his family in the stands to celebrate his win, leading to some of the most iconic images in tennis history being taken.
Nadal will also be participating at the 2024 Wimbledon's Championship.
Novak Djokovic vs Roger Federer (2019)
In more recent memory, one of the most epic matches of tennis ever played has to be the face off between Djokovic and Federer, which in many ways was reminiscent of the Federer Nadal match we just covered.
History Repeating
Just like Federer’s 2008 game against Nadal, this match was colossal, lasting even longer than the previous one. The match dragged on to a total of 4 hours and 57 minutes, making it once again the longest in tennis history.
Just like its predecessor, this match was a five set test of stamina, that saw both players refusing to give up and providing expert defences against each other's match points time after time.
In the end, the fifth set was decided by a historic first; a tiebreaker which was needed after the last game dragged on to 12-12. Djokovic managed to clinch the tiebreaker and win the match and consequently his 16th grand slam title, while denying Federer of his 21st.
Much like in the aftermath of the 2008 game, the titan of tennis had nothing but respect for his opponent, accepting defeat gracefully and complimenting the tenacity, skill and sportsmanship displayed by Djokovic.
Together with Nadal, Djokovic is one of the must-watch players in Wimbledon.

Afterword
Thank you for reading our article on the most iconic matches from the Wimbledon Championship. We hope that you either learned something, or enjoyed a refresher on the best moments from tennis history.
If you want to learn more about tennis, make sure to check out our other tennis related articles right here on the Superprof blog.
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We hope to see you again soon, Goodbye for now from the Superprof team!









