Ranking the 10 Most Iconic Moments in Wimbledon History

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With most of the favorites still in contention in this year's Wimbledon, a memorable moment may be in store. But will it match some of the most iconic moments in Wimbledon history?

We limited our rankings to the Open Era, because many of the earlier noteworthy occurrences are known to us only by reputation or through books. Many of us witnessed the iconic Wimbledon events in the Open Era, allowing us to relive those unforgettable bits of history in our mind's eye.

A number of iconic events that did not quite make our list deserve mention. They include the sixth Wimbledon meeting of the Williams sisters this year, the championship run of 17-year-old, unseeded Boris Becker in 1985, the female streaker who made an appearance on Centre Court just before the 1996 final, Steffi Graf's 1988 victory that was part of her Grand Slam year, Cliff Richard singing "Singin' in the Rain" on Centre Court during a 1996 rain delay and Rod Laver's triumph in the very first open Wimbledon in 1968.

Our list of the 10 most iconic moments in Wimbledon history is based on a subjective ranking of the images and occurrences that are most deeply etched into our minds, hoping to identify the events that will be discussed for years to come.

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Champions are supposed to go out on top. However, it is often more memorable if they depart in anguish.

Pete Sampras won seven Wimbledon titles, tied for the most in history, and he never lost a Wimbledon final. He and Roger Federer are the undisputed kings of the All England Club in the Open Era. Sampras had won four straight Wimbledon titles from 1997 through 2000, and his five-set, fourth-round loss to Federer in 2001 was hardly an embarrassing experience.

But Sampras' final match at the All England Club was a sad affair. His second-round contest of the 2002 Wimbledon took place not on Centre Court but on Court No. 2, a cramped stadium that is called the "Graveyard of Champions."

The 30-year-old Sampras was the No. 6 seed and still a major threat on grass. He was expected to handle an unknown named George Bastl with ease.

Bastl was ranked No. 145, not high enough to get entry into Wimbledon without going through qualifying rounds. He then failed to qualify, but got into the main draw as a "lucky loser" because someone had withdrawn with an injury.

Bastl won the first two sets, but Sampras charged back to win the next two, perhaps motivated by a note from his wife that he read during changeovers, according to the Telegraph. Sampras seemed destined for an amazing comeback that would add to his Wimbledon legend.

Instead, Sampras dropped the final set and lost, 6-3, 6-2, 4-6, 3-6, 6-4.

As Bastl tossed wristbands into the crowd, the stunned Sampras stayed seated for several minutes before walking off, head down.

Bastl lost 6-2, 6-2, 6-2 to David Nalbandian in the next round and never won another match in a Grand Slam event. In his last attempt to reach the main draw of a major, Bastl lost in the first round of qualifying for the 2009 U.S. Open, falling to 160th-ranked Roko Karanusic 6-0, 6-0.

After losing to Bastl, Sampras insisted he would return to Wimbledon the next year. He won the U.S. Open later that year for his 14th and final Grand Slam singles title, but he never played singles at Wimbledon again.

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Seldom does a first-round match between players ranked outside the top 15 stay locked in the memory banks. That is especially true when the match is played on Court 18 at the All England Club, far away from the hub of action, in a space that accommodates no more than 782 spectators.

But the 2010 Wimbledon matchup of John Isner and Nicolas Mahut was like no other tennis match at any tournament before or since.

Not surprisingly, Isner, who was ranked No. 19 at the time, prevailed over 148th-ranked Nicolas Mahut. The score was what made the match iconic. Isner won 6–4, 3–6, 6–7, 7–6, 70–68

The fifth-set score is not a misprint. It was indeed 70-68. To say it was the longest match in history is an understatement. The 138 games and the eight hours and 11 minutes used to play the final set alone were both far more than had been compiled in any previous match in history.

The fifth set had to be suspended twice because of darkness. By the calendar, the match lasted three days. By the stopwatch, the match lasted 11 hours and five minutes. 

By the time the match was suspended for the second day with the two tied at 59-59 in the final set, it was receiving worldwide attention. The scoreboard could not handle it, malfunctioning at one point in the fifth set.

When Isner finally broke serve in the 138th game of the fifth set, the two had played 980 points, including 215 aces (112 by Isner, 103 by Mahut). They had held serve in 180 of 183 games. The tennis itself was not particularly entertaining, but the sheer length of the match made it remarkable theater.

Mahut later wrote a book about the event titled The Match of my Life (La Match de Ma Vie).

And it could only happen at Wimbledon, which refuses to use a tiebreaker in the ultimate set.

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The way Jana Novotna lost the 1993 Wimbledon final, simply choking away a sizable lead against Steffi Graf, made that match noteworthy.

However, the iconic moment came during the awards ceremony afterward, as a member of British royalty comforted the loser during an outpouring of personal anguish. 

Novotna, the No. 8 seed, had upset Martina Navratilova in the semifinals, and seemed on the verge of knocking off defending champion Graf in the final. Novotna had won the second set easily and rolled to a 4-1, 40-30 lead while serving in the third set. Novotna then double-faulted, lost the game and never completely recovered. Novotna lost five straight games and was defeated 7-6, 1-6, 6-4 by Graf, who won her third straight Wimbledon title.

The 24-year-old Novotna, who had frittered away a chance for her first Grand Slam singles crown, was crushed.

When Novotna accepted the runner-up trophy from the Duchess of Kent, Novotna literally put her head on the Duchess' shoulder and openly wept, as the Duchess tenderly caressed the crestfallen runner-up. There was nothing contrived about the actions of the Duchess, who put her hand around Novotna's neck as naturally and tenderly as she would her own child at home.

Watch a video of the match and the award ceremony here and see if you can hold back tears.

By the way, Novotna won her one and only Grand Slam singles title at Wimbledon in 1998. The Duchess of Kent presented her with the winner's trophy.

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The drought was noted in other countries, but it was a major issue to British fans. Just as Boston baseball fans had bemoaned the fact that the Red Sox had not won a World Series since 1918, British tennis fans lamented the fact that no British male had won a Wimbledon singles title since 1936.

Andy Murray of Scotland, the best British hope in years, had lost to Roger Federer in the 2012 Wimbledon final. The pressure on Murray from his home country to win Wimbledon was mounting as he entered his final-round match against Novak Djokovic in 2013. You can get a taste of that pressure from this ESPN video.

The misery ended for Red Sox fans in 2004. For British tennis fans, the 77-year wait ended in 2013, when Murray won the Wimbledon title by beating Djokovic in straight sets.

As the BBC report on the match noted, "Murray was willed on by the majority of the 15,000 spectators on Centre Court, thousands watching on the nearby big screen and millions more around the country."

The Guardian put it this way: "It was one of those moments that will forever be bathed in a glow of palpable warmth, from the crowd and the skies above the opened roof of Centre Court."

It is probably no coincidence that Murray became so occupied by requests and publicity in the aftermath of that victory that he failed to reach the final in any of his next five Grand Slam events and got to the semifinals of only one of them.

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Three factors combined to make the 2001 men's final one of the most fascinating tennis events in history.

First of all, the atmosphere was unlike any seen at Wimbledon before or since. Rain had postponed the final from Sunday to Monday. As a result, 10,000 tickets were handed out on a first-come, first-served basis, giving the common man a chance to get a seat at Centre Court. People who had camped out overnight waited in a line that was miles long to get one of the tickets. It provided a very different kind of crowd from what the staid grounds of the All England Club were used to.

Centre Court was more like a zoo, with banners, flags and colorful clothing featured in a crowd that was boisterous throughout with partisan sections for each player. The Guardian called it "a football-style crowd" and noted, "The All England Club has never seen anything like it."

The second factor was that the final between Goran Ivanisevic and Pat Rafter was absolutely riveting, with the loud crowd riding every wave in the back-and-forth match. Rafter saved three match points in the final set, but Ivanisevic ultimately prevailed 6-3, 3-6, 6-3, 2-6, 9-7.

The third and final element was the shocking victory by Ivanisevic. A three-time Wimbledon finalist who had never won a Grand Slam singles title, Ivanisevic had virtually faded out of sight at the age of 29 in 2001.

Bothered by shoulder problems for the better part of two years, he was ranked 125th at the time and needed a wild-card entry just to get into the Wimbledon main draw. He had lost in the first round in four of his five tournaments immediately before Wimbledon, including three losses to players ranked outside the top 80.

Somehow he found the magic at Wimbledon, beating British favorite Tim Henman in five sets in the semifinals before closing out Rafter in another five-setter to become the first wild-card entrant to win Wimbledon. It was Ivanisevic's only Grand Slam singles title.

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Martina Navratilova did not care much for records. Seldom does she mention what is probably her most impressive accomplishment: the 74-match winning streak. However, she did care about one mark: most Wimbledon singles titles.

“I wanted the record, no doubt about it,” Navratilova told the Telegraph years later. “I was lucky enough to set a few records in my career, but they just happened because I played well for a long time, but when I realized I was in with a chance of breaking the Wimbledon singles record, it became a big goal of mine."

Navratilova won her first Wimbledon singles crown in 1978 at the age of 21. She won her eighth in 1987, tying the record set by Helen Wills Moody in 1938. Navratilova lost in the final to Steffi Graf in 1988 and 1989, and she was running out of time to capture that elusive ninth crown.

The 1990 Wimbledon was seen to be her last opportunity. She no longer dominated women's tennis. Three years and 10 Grand Slam events had passed without Navratilova winning a title in a major. And she was 33 years old.

There was also the matter of her knees.

"I was playing some of my best tennis on grass that summer, but I was pretty concerned about my knees," Navratilova told the Telegraph. “I would wake up in the morning not knowing if they would be OK or not. Five months after Wimbledon, just before the big end-of-the-year tournament, they locked really badly and I had to go into hospital for an operation."

Navratilova not only won the 1990 Wimbledon for her record ninth title, but she had one of the most dominating performances of her career. She did not come close to losing a set in her run to the championship. Zina Garrison, who had done Navratilova a favor by beating Graf in the semifinals, was no match for Navratilova in the final. 

"She really believes this is her court and that no one can take it away from her," said Garrison, according to ESPN.com, after Navratilova handed her a 6-4, 6-1 defeat.

Four years later, at the age of 37, Navratilova reached the Wimbledon singles final again, only to lose in three sets to Conchita Martinez. Had she won title No. 10, that moment might rank as the most iconic moment in Wimbledon history.

The 1990 Wimbledon crown was Navratilova's final major title, but it made her the oldest woman to win a Grand Slam singles event, a mark Serena Williams would break if she wins Wimbledon this year.

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It's not poetry worthy of Frost or Whitman, but John McEnroe's outburst directed at the elderly chair umpire during a 1981 Wimbledon first-round match may be the most famous on-court quote in tennis history.

"You can't be serious, man. YOU CANNOT BE SERIOUS. That ball was on the line. Chalk flew up. It was clearly in. How can you possibly call that out? He's walking over. Everybody knows it's in in the whole stadium. And you call it out? (Pause) You guys are the absolute pits of the world, you know that?"

Chair umpire Edward James hit McEnroe with a penalty point.

That tirade obscured the fact that McEnroe would go on to win the Wimbledon title that year, beating Bjorn Borg in the final to end Borg's five-year run as champion.

Trivia question: Who was McEnroe's opponent in that first-round match? Only the dedicated tennis fan knows it was Tom Gullikson, who would lose the match in straight sets.

A 2011 story in the Telegraph reported that fans in 2010 voted McEnroe's rant as their top Wimbledon moment of all time.

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Jimmy Connors was considered almost unbeatable in 1975, especially on grass. He had beaten Ken Rosewall in the final of the 1974 Wimbledon 6-1, 6-1, 6-4 and had crushed Rosewall again in the final of the 1974 U.S. Open (then played on grass) 6-1, 6-0, 6-1.

Although he had lost in the final of the 1975 Australian Open to John Newcombe, the top-seeded, 22-year-old Connors was at the top of his game at Wimbledon that year, reaching the final without the loss of a set.

Meanwhile, the 31-year-old Arthur Ashe seemed to be past his prime. He had won the 1968 U.S. Open and the 1970 Australian Open but had not gone past the quarterfinals of a major since reaching the final of the 1972 U.S. Open.

Ashe, the No. 6 seed, made his way to the 1975 Wimbledon final, but it had been a struggle. He had to go five sets to get past No. 16-seeded Tony Roche in the semifinals.

Not only was Connors an overwhelming favorite against Ashe, but Connors was a prohibitive 9-10 favorite to win in straight sets, according to an ESPN.com article on the match.

Adding to the flavor of the match was the fact that the quiet, gentlemanly Ashe and the young, brash Connors were not friends. Just two weeks earlier, Connors had announced a $5 million libel suit against Ashe for criticizing Connors' decision not to play for the U.S. Davis Cup team.

Connors was expected to take his anger out on Ashe, who wore his USA Davis Cup jacket during the warm-up for the match.

However, Ashe had a strategy that minimized Connors' effectiveness. Ashe used dinks, chips, lobs and short angles to blunt Connors' powerful groundstrokes.

Ashe recalled his approach in a 2010 article in the Telegraph:

"The plan was that if I got into a rally from the baseline, I had to hit the ball with no pace, with underspin and down the middle to land around the T junction so he would have to come into the court and, with his very flat strokes, would have to hit up on the ball, wouldn’t be able to hit it hard and so would have to compromise.”

Ashe not only won, but he won decisively, 6-1, 6-1, 5-7, 6-4, for one of the most shocking upsets in a Wimbledon final.

The match was also historically significant, as Ashe became the first (and still the only) African American male to win Wimbledon.

It was Ashe's final Grand Slam singles title, and the match became even more iconic when Ashe tragically died at the age of 49 after contracting HIV from a blood transfusion during heart surgery. He was awarded the Presidential Medal of Freedom posthumously by President Bill Clinton for his humanitarian work.

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Often called the greatest tennis match in history, Rafael Nadal's 6-4, 6-4, 6-7 (5-7), 6-7 (8-10), 9-7 victory over Roger Federer in the 2008 Wimbledon final featured the added dramatic elements of two rain delays and a finish that was shrouded in darkness.

ESPN proclaimed it the most memorable Wimbledon final in the Open Era, and L. Jon Wertheim wrote a book about it titled, Strokes of Genius: Federer, Nadal, and Greatest Match Ever Played.

The drama for the 2008 match had been building for two years. Federer beat Nadal in four sets in the 2006 Wimbledon final and outlasted him again in five riveting sets at the All England Club climax in 2007.

As the New York Times noted after the 2008 epic, "Last year’s emotional tussle immediately took its place among the best Wimbledon finals, but this five-set classic—played on a rainy, gusty day—was better yet."

Heading into the 2008 final, Federer had not lost a match at the All England Club since 2002 and was shooting for his sixth straight Wimbledon crown. Nadal, already known as the king of clay, had been getting better on grass year by year and was finally in position to beat the man who had ruled grass-court tennis for years.

The tennis was of the highest caliber as the No. 1 and 2 players in the world tried to establish dominance with their contrasting styles. In the engrossing fourth-set tiebreaker, Federer fought off a pair of match points against him, the latter on a breathtaking backhand passing shot.

Federer won the tiebreaker 10-8 to even the match, but Nadal ultimately prevailed to earn his first Wimbledon title.

The match lasted four hours and 48 minutes, the longest singles final in Wimbledon history, and ended at 9:16 p.m. local time. By then darkness was starting to descend on the Centre Court, and there was little natural light for the award ceremonies as the flash bulbs of cameras illuminated the night. 

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The 18-16, fourth-set tiebreaker in the 1981 Wimbledon final may have been the most riveting 22 minutes in tennis history.

The contrasting styles and personalities of the participants made it an enthralling matchup from the start: No. 1-ranked Bjorn Borg—the cool, stoic Swede with the breathtaking groundstrokes—was up against No. 2-ranked John McEnroe—the loud, combative American with the masterful serve-and-volley game. The appeal of the Borg-McEnroe matchup went far beyond the confines of the tennis world.

After McEnroe cruised through the first set, Borg won the next two and let a double match point slip away while serving at 5-4, 40-15 in the fourth set. Each held serve one more time to force the tiebreaker.

The drama already present when the tiebreaker began seemed to build with each point, as the decider went on and on. The pair changed sides five times during the tiebreaker, and they even forgot to change when it hit 15-15. You could feel the tension in the crowd increase with every winner and every error. 

Borg had five match points in the tiebreaker and McEnroe had six set points before he captured the fourth set on his seventh set-point opportunity when Borg netted an easy forehand volley.

Despite losing the 34-point tiebreaker, Borg rallied to win the fifth set and the match 1-6, 7-5, 6-3, 6-7 (16-18), 8-6 for his fifth straight Wimbledon crown. Borg was just a month past his 24th birthday and he had just won his 10th Grand Slam singles title. Astonishingly, he would win just one more major, the 1981 French Open.

It is worth noting that the dramatic 1980 tiebreaker that defined the Borg-McEnroe rivalry could not have occurred in the fifth set, as Wimbledon does not utilize a tiebreaker in the fifth set of men's matches.

Whether the 1980 final was the greatest Wimbledon match in history is open for debate, but the legend of that 22-minute tiebreaker stands alone.