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Ranking the Top 10 Tennis Matches in Wimbledon History

| June 19, 2022 1:49 pm PDT
Best Wimbledon Matches

Wimbledon is the oldest tennis tournament on the planet, with its first edition held in 1877. So far, there’ve been 134 editions of the event in total. The tournaments held within the last couple of decades have had 675 matches each.

What this means is that nearly 100,000 matches have been played at Wimbledon as of 2022. That said, picking out the very best Wimbledon matches isn’t easy. However, there are some that stand out from the crowd.

Some of those are Cinderella stories that saw major underdogs defeat huge favorites. Others are important for being clashes of tennis giants. Then, there are some matches that saw the players break some important records.

So, which matches are those? Below is my selection of the top 10 Wimbledon matches in the history of the tournament.

Each of these is important for a specific reason, but they all have one thing in common – they’re all among the most thrilling Wimbledon matches ever. A lot goes into knowing how to bet on Wimbledon, and learning about the history of the tournament is a big piece to that puzzle.

To aid your cause, let’s dive into the greatest matches in Wimbledon history.

10. Virginia Wade vs. Betty Stove (1977)

The year 1977 was a fantastic year for Brits. Queen Elizabeth celebrated her Silver Jubilee, rock band Queen released their We Are the Champions/We Will Rock You single, and Virginia Wade became the Wimbledon champion.

Wade did it by beating Dutch player Betty Stove in the final, thus becoming the first British player to win the ladies’ singles championship in 11 years. By doing that, she also became the first British woman to win a Grand Slam in the Open Era.

Even more importantly, Brits had to wait another 35 years before getting another Wimbledon champion – Andy Murray finally broke the spell in 2013.

9. Roger Federer vs. Pete Sampras (2001)

When he qualified for the 2001 Wimbledon, Roger Federer was just 19 with no major titles in his portfolio. In fact, his previous two adventures at SW19 ended in Round 1.

Everyone was expecting something similar to happen in the 2001 tournament, especially when it became clear he was going to face then world no.1, Pete Sampras, in the fourth round.

Sampras, who had previously won four Wimbledon titles in a row, was expected to cruise past Federer, but the Swiss ended up claiming a big win in one of the best Wimbledon matches ever.

Both players started strong, with Federer winning the first set after a tiebreaker (9-7). Sampras fought back, winning the next set 7-5. Federer then made it 2-1 in sets, winning the third set 6-4 without any major problems. Sampras bounced back again, winning the next set. It wasn’t easy, though. The American won only after a tiebreaker (7-2).

What this meant was that the two had to play one final decisive set. The fifth set too lasted for a long time, with both players giving all they got on the grass court of All England Club. Eventually, it was Federer who triumphed 7-5.

The win over the best player in the world at the time put the Swiss in the spotlight. However, it didn’t last too long – Federer’s 2001 Wimbledon journey finished in the following round where he lost to Tim Henmann 3-1 in sets.

It took Federer another two years before he finally won his first Grand Slam tournament. From there, he went on to win another 19 majors.

More than two decades after the Sampras match, Federer is considered one of the best players in the world, especially when it comes to playing on the grass court.

With eight Wimbledon titles in his collection, he remains the most successful player in the history of the tournament.

8. Andre Agassi vs. Doug Flach (1996)

The reason why this match deserves to be on the list of best Wimbledon matches in history is that it saw one of the biggest upsets in the history of tennis.

It was the first round of 1996 Wimbledon, which had a lineup packed with superstars. One of those was Andre Agassi, who came to England as the third seed. His first opponent was unseeded player Dough Flach, who, at the time, was sitting in the #281 position in the ATP Rankings.

It’s needless to say that Agassi was a huge favorite to demolish his opponent. However, the exact opposite happened – Flach beat his much more famous rival.

7. Chris Evert vs. Martina Navratilova (1978)

The biggest rivalry in women’s tennis in the 1970s was the one between Chris Evert and Martina Navratilova. The rivalry saw two worlds collide – on one side, there was Navratilova with her aggressive serves and volleys; on the other, there was baseliner Evert.

It all started in 1973 with Evert winning 21 of their 25 duels over the following five years. The rivalry reached its peak at the 1978 Wimbledon, which is when the tied turned in Navratilova’s favor.

Navratilova defeated her foe in the final, thus ending Evert’s reign as the world no.1. After three sets packed with excitement on both sides of the net, Navratilova ended up winning her first major title.

6. Jimmy Connors vs. Arthur Ashe (1975)

After winning three Grand Slam tournaments in 1974, Jimmy Connors was the #1 favorite to pull off something similar the following year. The title slipped from his hands in Australia, but he was determined not to let the same happen at Wimbledon.

Connors entered the tournament in top gear, reaching the final without dropping a single set along the way. Then, the final came, where he went toe-to-toe with his fellow American, Arthur Ashe.

Ashe, who’s nine years Connors’ senior, wasn’t expected to do much in the final. After all, his career was on a downward path in the months leading to the 1975 Wimbledon. However, he shooshed his critics straight away by winning the first two sets, each by 6-1.

Connors fought back in Set 3, winning 7-5. However, Ashe rose from the ashes in the fourth set, winning by 6-4 in games, getting ahold of his first-ever Wimbledon trophy. Ashe’s triumph was important for another reason – he became the first black player to win this Grand Slam.

5. Bjorn Borg vs. John McEnroe (1980)

Bjorn Borg came to All England Club in 1980 as the defending champion, who won the previous three editions of Wimbledon. He entered the tournament as the #1 seed, meeting the expectations by cruising to the final where he was met with his arch-rival John McEnroe.

Dubbed the “fire and ice” rivalry, the Borg-McEnroe is still thought of as one of the biggest rivalries in the history of tennis. If you’re wondering why the media gave it that nickname, it’s because Borg was famously cold as ice, while his rival was known for his fiery temperament on the court.

Their rivalry reached the melting point in the 1980 Wimbledon final, which saw the two exchange shots for nearly four hours in a five-set battle. Bjorg was the one who won the match, but only after an 8-6 tiebreaker in the final set.

4. Andy Murray vs. Novak Djokovic (2013)

In 2011, Novak Djokovic won his first Wimbledon. Two years later, he was the #1 favorite to add another trophy to his collection. It seemed that the top tennis sportsbooks were right to favor the Serbian player, especially after his two main rivals got knocked out – Nadal lost in Round 1, while Federer’s journey ended after only two matches.

Although Djokovic did struggle in a couple of matches, his road to the final was relatively easy. And in the final, he was expected to have a field day against Andy Murray. However, boosted by his fans, Murray managed to pull off a major upset.

Murray beat Djokovic 3-0, becoming the first Brit to win the gentleman’s singles tournament at Wimbledon after Fred Perry in 1936. He also became the first Scottish player to win the title in 107 years. Before him, there was Harold Mahony who did it in 1896.

3. Novak Djokovic vs. Roger Federer (2019)

Two of Novak’s Wimbledon adventures made it to my list. His clash with Roger Federer in the final of the 2019 tournament definitely belongs on the list of the most intense Wimbledon matches ever. Actually, this match has all the ingredients needed to be called one of the greatest tennis matches in history.

What makes it saw awesome is that it lasted just three minutes short of five hours, which makes it the longest Wimbledon final to date. The clash between the two GOAT candidates saw five sets in total, with Djokovic grabbing a win in the end.

Not only was this a nerve-wracking duel, but the match is interesting for another reason. Federer outplayed Djokovic in almost every statistic but still failed to win. Some of those stats include:

Novak and Federer
  • A better first-serve percentage (62.6% Federer, 62.1% Djokovic)
  • A better second-serve percentage (51.3% Federer, 47.0% Djokovic)
  • More aces served (25 Federer, 10 Djokovic)
  • More break points (53.8% Federer, 37.5% Djokovic)

In fact, the only category in which Djokovic was better was unforced errors. Djokovic’s tally was 52, while Federer made 10 more.

2. John Isner vs. Nicolas Mahut (2010)

The first-round match between John Isner and Nicolas Mahut in the 2021 Wimbledon gentleman’s singles still holds the record for the longest tennis match in history. Contested over three days, its total playing time is 11 hours and 5 minutes.

The match saw five sets, with the final set taking eight hours and 11 minutes to finish after going to a tiebreaker that Isner won 70–68. It was such an extraordinary situation that even the scoreboard malfunctioned at one point – when the score was 47-47 in the fifth set.

1. Roger Federer vs. Rafael Nadal (2008)

Ranking the best Wimbledon matches would be incomplete without mentioning the 2010 Wimbledon final. It was a clash between two players who, at the time, were the best on the planet – Roger Federer and Rafael Nadal.

The proof is that the two had collectively won 14 of the previous 16 majors. Seven of those wins happened at Wimbledon, with Federer winning every one of them, beating Nadal in two finals. It was time for the Spaniard to strike back!

Bookmakers didn’t have much faith in Nadal, not just because of Federer’s dominance. It’s also because the Spaniard was switching from the slow clay courts of Roland Garros to the fast grass of All England Club.

The weather played an important role in the final, causing the tournament organizers to delay the match and suspend play in the third set. Eventually, the match lasted over seven hours, with the two finalists spending four hours and 48 minutes on the court. After a fierce battle in five sets, Nadal was the one to triumph, beating his rivals 3-2 (6–4, 6–4, 6–7(5–7), 6–7(8–10), 9–7).

“The best tennis match I’ve ever seen in my life” – that’s what Bjorn Borg said after the match, and I agree with him. Not only do I think this is the best Wimbledon match in history, but it also could be the greatest match in the history of the sport.

These are the best tennis matches we’ve seen, but what about the top rallies in tennis history? I’ve got you covered in the post below.

Ranking the 9 Most Epic Rallies in Tennis History

If you’re not familiar with the term, a tennis rally is a series of back-and-forth shots between the players which ends when one of them scores a point. Usually, rallies last up to four shots, with only a small percentage having 10+ exchanges. In fact,...

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Zarko Naric
Zarko Naric

Zarko Naric – the World's Greatest Sportswriter, according to his grandma.

Zarko started writing for GamblingSites.com in 2019, covering sports like soccer, tennis, and basketball,  as well as some more niche sports like cycling, for example.

In addition to writing news, picks, and blog pieces focused on sports, Zarko’s also been covering politics, TV/music contests, and so on.

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