US Open Tennis: The 10 Greatest Matches of All Time

Thomas SkuzinskiContributor IIISeptember 2, 2011

US Open Tennis: The 10 Greatest Matches of All Time

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    Some of the greatest matches of the open era have been played at the US Open. From Louis Armstrong Stadium to Arthur Ashe Stadium, the show courts at Flushing Meadows have served as stages to high drama. 

    Thrilling baseline exchanges. Aggressive serve and volley. Swings not only of rackets, but of momentum and emotions.

    These showdowns were notable both for what transpired on the court and for what they meant for the history of tennis.

    In the following video slideshow, relive the fierceness of rivalry, the unbridled confidence of youth and the dogged determination of old age.

Pete Sampras vs. Andre Agassi, 2001 Quarterfinal

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    The scoreline: Sampras, 6-7 (7-9), 7-6 (7-2), 7-6 (7-2), 7-6 (7-5)

    Why it mattered then:

    Sampras hadn't won a slam in more than a year. He had suffered a tough loss at the previous US Open final to Marat Safin, and at Wimbledon 2001 his 31-match tournament winning streak was famously broken by a young man named Roger Federer. Retirement rumors were getting louder and louder. 

    Agassi had won the Australian Open earlier in the year and was in the hunt for the No. 1 ranking, the continuation of a rebirth that had started in 1999. The two had only met three times in 2000 and 2001, all on hard courts, and Agassi had won all three.

    The match highlighted why we loved the Sampras-Agassi rivalry. Two contrasting personalities, with contrasting playing styles. One a great server and volleyer, the other a great returner and baseliner. In this match, each man was at his best, and each was committed to his preferred playing style. 

    At the start of the fourth set, the two veterans received a lengthy standing ovation that would bring a tear to the eye of even the most hardened observer. 

    Why it matters now:

    Serve and volley is largely a lost art, one employed only rarely and hardly effectively. In this match, we saw the clearest lesson that, all else being equal, a serve-volleyer would always triumph over a baseliner.  

Martina Navratilova vs. Chris Evert, 1984 Final

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    The scoreline: Navratilova, 4-6, 6-4, 6-4

    Why it mattered then:

    From 1982 through 1984, Navratilova was riding a wave of dominance that included only six losses and eight grand slam titles. Imagine a season like the one being enjoyed by Novak Djokovic. Now imagine it happening three years in a row. Martina swept Evert aside during much of this time, and this included wins in the 1984 French Open (Evert's favored surface) and Wimbledon.

    On paper, few would have expected much of a match from Chris Evert in the face of this dominance. But Evert had been improving her fitness, serve, and weight of shot, and had a massively supportive New York crowd in her favor.

    Navratilova was not her best that day by her own ridiculously high standards, but after winning the opening set Evert failed to take advantage of several chances to shut the door on her opponent.

    The match was a snapshot of the second half of the Evert-Navratilova rivalry that had started 11 years earlier. Where Evert once dominated, in later years she seemed to always be chasing the more physical, more aggressive Navratilova.

    Why it matters now:   

    This match is a perfect complement to Sampras and Agassi: another example of two veteran champions, with contrasting personalities and contrasting styles. It's another lesson about the viability of an athletic, serve-volley game. Yes, even in today's game. 

John McEnroe vs. Jimmy Connors, 1980 Semifinal

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    The scoreline: McEnroe, 6-4, 5-7, 0-6, 6-3, 7-6

    Why it mattered then:

    Think about the respect and gentlemanly friendship between rivals Roger Federer and Rafael Nadal. The rivalry between Jimmy Connors and John McEnroe was the exact opposite. Their battles never ended in hugs or words of comfort. They ended in bruising victory and bitter defeat.

    The 1980 clash had plenty of build up behind it. The two had already met 13 times and had evenly split their contests at majors. Semifinal meetings at the US Open had become a small tradition, with Connors winning in 1978 and McEnroe getting revenge in 1979. The two, with Borg, were in a battle for the No. 1 ranking.

    Connors was hot in the second and third sets, even managing a rare bagel against McEnroe, but McEnroe righted the ship and barely survived.

    Over the next four years McEnroe would be dominant enough to claim the year-end No. 1 ranking from 1981 to 1985. Connors, despite being past his prime, would still claim three more grand slam titles, including two at the US Open and a measure of revenge against McEnroe at Wimbledon.

    However, in all subsequent meetings between the two most famous hotheads in tennis, the quality was never quite what it was that evening in 1980 in front of a New York crowd. 

    Why it matters now:

    Connors and McEnroe gave us the first tennis rivalry built on public animosity, and honestly that's not something from which you can learn much. It's dramatic and fun and occasionally crazy, but it's best when it's channeled into tennis.      

John McEnroe vs. Bjorn Borg, 1980 Final

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    The scoreline: McEnroe, 7-6, 6-1, 6-7, 5-7, 6-4

    Why it mattered then:

    McEnroe provided us with not one but two epic matches, and both were in the same tournament.

    This final fell in the shadow of what was, and to some still is, the greatest match of all time, between Borg and McEnroe at Wimbledon in 1980. That match was won by Borg in dramatic fashion, including an 18-16 tiebreak in the fourth set and an 8-6 fifth set. It was epic.

    Less often remembered is the final from later that summer, which also went five sets. Borg served for the first set twice, and losing it seemed to cloud his concentration through the second set and start of the third. McEnroe seemed on the verge of a hard-fought, straight-sets win. But as expected, Borg raised his level of play just in time.

    Consider that Borg had not lost a fifth set since 1974, that he was the dominant player and had two legs of the grand slam completed (for the third straight year). Consider that both players had survived tough five setters the day before. Perhaps it was inevitable that the final could not quite live up to the sustained quality of Wimbledon, but under the circumstances perhaps its quality was more remarkable.    

    It was a turning point in the Borg-McEnroe rivalry, and the subsequent dominance of McEnroe in 1981 would spur Borg into an early retirement. Borg would never win the US Open, despite four finals appearances.

    Why it matters now:

    Sometimes in sport, and in life, we're confronted with an obstacle of considerable size and weight. Borg was that obstacle for McEnroe, and McEnroe's response to the challenge was inspiring. Rather than also raise his level again, Borg's response to his inability to find an answer to McEnroe was to walk away from the game. More than injury and age, pride can often be the biggest adversary to a tennis player. Perhaps the greatest achievement in any sport is simply sticking around, even if it seems your time has passed, simply for your love of the game and the fans. 

Martina Navratilova vs. Steffi Graf, 1991 Semifinal

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    The scoreline: Navratilova, 7-6, 6-7, 6-4

    Why it mattered then:

    The 1991 US Open yielded the greatest single day of women's tennis in history, not just at the US Open but in all of tennis. The stakes were high, the anticipation was off the charts, and somehow the matches still surpassed expectations. 

    Graf was trying to regain her form at the 1991 US Open, having definitively ceded the position of dominance to Monica Seles. Many of Graf's remarkable streaks had ended in the past two seasons, including 186 weeks at No. 1, 13 grand slam singles finals and five years of reaching the semifinals or better in grand slams. A US Open win would re-establish Graf following a victory that year at Wimbledon and would help silence discussion of her injuries and personal problems.

    Navratilova was 34 and also trying to regain a foothold in the women's game. Not only had Graf eclipsed her, but 15-year-old Jennifer Capriati had knocked her out at Wimbledon in the quarterfinals, Navratilova's earliest exit in 14 years. Most thought Martina was past her prime, especially on hard courts, and that Steffi would handily earn her 500th win.

    But it wasn't to be. Martina proved that age really is just a number, playing a nearly flawless version of her serve and volley game. The match was about tactics and steely resolve as much as it was about the physics of the game, and most consider it among the top five women's matches of all time.

    Why it matters now:

    When did you last see a women's match between a great serve-volleyer and an artist who could viciously slice and dice? Martina's approaches to the net and Steffi's slice backhand would still frustrate most of the women on the tour today. Despite this obvious vacuum, we still see little variety among the younger generation. 

Monica Seles vs. Jennifer Capriati, 1991 Semifinal

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    The scoreline: Seles, 6-3, 3-6, 7-6 (7-3)

    Why it mattered then:

    We like to think of this match as the fairy tale breakthrough of a young phenom, but Capriati was already firmly established in the top 10 and was seeded seventh at the Open. She had reached the 1990 French Open semifinals, losing to Seles, and the 1991 Wimbledon semifinals, losing to Gabriela Sabatini. Seles was another step up, but a battle was expected between the two teenagers.

    Seles was attempting to reclaim the No. 1 ranking she had captured from Graf earlier in the year and was gunning for her third grand slam crown of the year. Everyone knew that Seles was the best player, and now she needed the stamp of approval of a year-end No. 1 ranking.

    After Seles shot out to a 6-3, 3-1 lead, the match was still merely on the simmer and a relatively straightforward Seles win seemed likely. But Capriati found a new level, won the next five games, and sent the match to one of the more captivating third sets ever played.

    It wasn't often pretty, and that's what made it beautiful. 

    Contrasted with the styles of Graf and Navratilova, Seles and Capriati offered a one-dimensional but remarkably effective power game. It was built on precision, penetration and a penchant for taking the ball early and on the rise. Watching this match, you had the feeling that a new era had arrived. 

    Why it matters now:

    Twenty years later, the new era continues. With the exception of a small blip in the trend named Martina Hingis, and a smattering of crafty French Open winners, women embraced a game built around flat groundstrokes and two-handed backhands. The scary thing is that few women are as good at employing this tactic as were Capriati, Seles, Davenport, Henin, Clijsters and the Williams sisters. Without them to compete against each other, we're left with a hollowness in the women's game.   

Jimmy Connors vs. Aaron Krickstein, 1991 Fourth Round

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    The scoreline: Connors, 3-6, 7-6 (10-8), 1-6, 6-3, 7-6 (7-4)

    Why it mattered then:

    Few remember that Aaron Krickstein would have been a worthy competitor for even the dominant players of his era. He had reached the US Open semis two years earlier and would reach the Australian Open semis in 1995. Injuries ultimately kept him from realizing his full potential, but few thought a win by Connors was probable, much less a five-set win over a much younger opponent.

    Jimmy Connors hadn't won a slam title in eight years, and he was playing with a rebuilt wrist and the lingering effects of a bevy of injuries that would have flattened a battalion of tennis players. But Connors was a one-man army.

    He had shown flashes of brilliance at the other slams that year and had already come back against Patrick McEnroe from being two sets and 3-0 down. The Krickstein match would happen on Connors' 39th birthday, and the amazing crowd support would carry him through the match, giving him not only a second wind but probably a third, fourth and fifth. They cheered his temper and his heroics, and by the fifth set one sensed that no matter how close Krickstein might come it was not to be his night. Before the fifth-set tie break Connors famously spoke into the camera: "This is what they came for. This is what they want." 

    Connors made it to the semifinals that year, losing finally to Jim Courier in straight sets. He would play other grand slam matches, but most regard this tournament as his farewell, a moment of affection shared between himself and the fans. 

    Why it matters now:

    Maybe 1991 was the season of proving that age is a construct, with Navratilova also continuing her winning ways. But Connors' victories were not just about age. He was plagued with injuries and health issues and never seemed to be the paragon of fitness. What Navratilova did was amazing but somehow made sense; it was the product of a great mind working with a great body. What Connors did defied reason. His body should never have been able to do what it did, but his spirit was indomitable. How lucky we would be if every player had that spirit.  

Justine Henin-Hardenne vs. Jennifer Capriati, 2003 Semifinal

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    The scoreline: Henin-Hardenne, 4-6, 7-5, 7-6 (7-4)

    Why it mattered then:

    Capriati appears twice on the list, and at two wildly different moments in her career. After bursting onto the scene at a very early age, Capriati became her own worst enemy and never quite fulfilled that young promise until a decade later. In 2001 and 2002, she won three grand slam titles and held the No. 1 ranking at times. The promise seemed fulfilled. However, she had never reached a US Open final.

    Henin-Hardenne had announced her arrival earlier in the year at the French Open, consolidating a steady rise in the rankings the last two seasons. At the US Open, she was seeded second behind fellow countrywoman Clijsters. Justine compensated for her smaller frame with determination and an attacking instinct. The world was already aware of her powerful offense, with a one-handed backhand that remains the best ever and a forehand that was equally potent.   

    The match was remarkable and arguably one of the highest quality women's matches ever played. From the first points, you could sense that both players were in peak form, and that neither was willing to give an inch. Capriati threw some heavy punches that night and was two points away from victory an astonishing eleven times. But Henin-Hardenne never blinked and was the last one standing, albeit barely, after three hours. She somehow recovered to win the women's final the next day against Clijsters and would finish the year at No. 1. 

    Capriati had one more chance at a US Open final the next year against Elena Dementieva but once again fell short. It was her fourth loss at that stage in the tournament.

    Why it matters now:

    The conventional logic in tennis is that size matters. While this might be true most of the time, Henin was the template for making the most of every inch and pound that she has. Tennis is a physical sport, but it's also about tactics and tenacity. Where Hingis crumbled when faced with bigger, stronger players, Henin rose to the challenge. Players of every shape and size should follow that example. Her retirement examples? Not so much.    

Serena Williams vs. Venus Williams, 2008 Quarterfinal

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    The scoreline: Serena, 7-6 (8-6), 7-6 (9-7)

    Why it mattered then:

    After a period of dominance from 2000 to 2003, the Williams sisters' stars had faded considerably.

    Serena had been slowly recovering in the rankings since 2007, after ending 2006 ranked 95th. At the US Open she was ranked fourth and was finally firmly in the hunt once again for the No. 1 ranking, a result that few of the experts had anticipated in 2006 when she was earning many critics.

    The story had been similar for Venus, who was barely within the top 50 in 2006. However, Venus had also been on the rise. The two had met in the Wimbledon 2008 final, where Venus broke a string of grand slam losses to her sister from years earlier.

    This was their first meeting at the US Open in five years, and it coincided with them both being in top form. The result? Two hard-fought sets, both comebacks by Serena who saved a total of 10 set points that night and in both sets came back from being down a break. After having a bevy of Williams sisters clashes that failed to live up to their potential, this match was the first and only time that Venus and Serena seemed to play purely as incredibly talented professionals and champions.

    Serena would go on to win the tournament and other slams. Venus has not won a slam since Wimbledon 2008. 

    Our only regret about this match? That it was a quarterfinal and was relegated to coverage on a cable network. Because of that, it rarely enters our conversations about the greatest US Open matches.

    Why it matters now:

    Following a year of injury in 2011, it was already unlikely that Venus would be able to return to the form displayed in 2008. With the revelation about Sjogren's syndrome, some are prematurely dismissing her from tennis. We'll surely keep seeing Venus and Serena on the courts, maybe even against each other, but never again at this quality. With the lack of raw power and talent in women's tennis, except for Serena at the moment, we might be waiting a few seasons to see this brand of tennis again.    

Mats Wilander vs. Ivan Lendl, 1988 Final

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    The scoreline: Wilander, 6-4, 4-6, 6-3, 5-7, 6-4

    Why it mattered then:

    The longest final in US Open history featured the classic story of a king hoping to retain his last stronghold against the usurper. In 1988, we saw Lendl, the three-time defending champion, trying to hold off Wilander, the man who had claimed titles at Roland Garros and the Australian Open that year.

    By the time the Open arrived, both men held six grand slam titles. Lendl was hotter in the rivalry, holding a six-match winning streak over the past three seasons that included the French Open and US Open in 1987. But Wilander was hotter on the season, going for his third slam title that year and chasing the elusive No. 1 ranking.

    The match was a strange combination of marathon, slow dance and water torture. Many rallies lasted more than 30 shots, many games went to deuce multiple times and each man exhibited a remarkable patience and cool-headed demeanor. Both players seemed to be in a bubble. Wilander's briefly burst when he was called for taking too long to serve in the second set when up 4-1, but he would finally gather his wits in the third set and rode out the rest of the match's many ups and downs from there.

    With Edberg's win at Wimbledon and Wilander's trifecta of victories, 1988 became the year of the "Swedish slam" and finally brought home a US Open title that countryman Borg had been so close to winning. 

    Why it matters now:

    The message of the match was delivered the following season. After claiming No. 1, Wilander was still only 25 but had seemingly lost all motivation. He would finish that season ranked No. 12 and would never win another grand slam. Imagine if Nadal had fallen off the map after Wimbledon 2008, and you'll start to appreciate the suddenness of Wilander's collapse. It was a lesson on the importance of always finding new motivation and never coasting on past achievement, a lesson with which many players still struggle.