Ranking the 10 Greatest Matches in US Open Tennis History

Jake Curtis@jakecurtis53Featured ColumnistAugust 31, 2013

Ranking the 10 Greatest Matches in US Open Tennis History

0 of 10

    Three riveting matches the previous two years rate consideration when ranking the 10 greatest matches in US Open tennis history.

    Serena Williams' three-set victory over Victoria Azarenka in last year's women's finals, Andy Murray's triumph over Novak Djokovic in the five-set 2012 men's final, and Djokovic's win in five sets over Roger Federer in the 2011 semifinals all provided compelling tennis.

    However, just one of those matches made our top-10 list.

    Only matches that took place in the Open Era, which began in 1968, were considered. The rankings were based on the quality of tennis, the drama of the match, the star power of the participants and the significance of the contest.

    Here's our countdown of the 10 greatest US Open matches.

10. Manuel Orantes vs. Guillermo Vilas, 1975 Semifinals

1 of 10

    For some reason, Manuel Orantes' amazing comeback in his 4-6, 1-6, 6-2, 7-5, 6-4 victory over Guillermo Vilas in the 1975 semifinals usually gets overlooked in discussions of great US Open matches.

    Perhaps it's because neither player is American. Perhaps it's because Orantes was overshadowed in that era by Bjorn Borg, Jimmy Connors, John Newcombe and others. Perhaps it's because few saw this match, which took place late at night with no television coverage. It's difficult to find any video of the match online, although brief clips are available here.

    It should have attracted plenty of attention because these were two of the best clay-court players in the world at the time, and the US Open was being played on clay (albeit the gray-green Har-Tru clay) for the first time.

    It was also the first time a Grand Slam event featured night sessions, and the contest between No. 2-seeded Vilas and No. 3-seeded Orantes went late into the night. Despite featuring long rallies between two baseliners, the match looked like it would end at a reasonable hour when Vilas won the first two sets, then held a 5-0 lead in the fourth. 

    Vilas had a match point at 5-0, but Orantes stunned the Argentine by playing serve-and-volley on that point, putting away his first volley to stay alive. Vilas had two more match points on his serve at 5-1, but Orantes saved both. In all, he saved five match points in the fourth set while winning seven straight games to capture the set 7-5.

    By the time the Spaniard finished off the fifth set and got back to his room, it was 2 a.m. About 18 hours after completing his grueling semifinal match, Orantes returned to the court against top-seeded Jimmy Connors.  

    Orantes showed no signs of physical or emotional fatigue as he blew by Connors 6-4, 6-3, 6-4 for his only Grand Slam title.

9. Novak Djokovic vs. Roger Federer, 2011 Semifinals

2 of 10

    Novak Djokovic produced one of the greatest clutch shots in history while beating Roger Federer 6-7, 4-6, 6-3, 6-2, 7-5 in the 2011 US Open semifinals.

    For the second straight year, Djokovic saved two match points while beating Federer in the Open semifinals. He had fought off two match points while serving at 5-4 of the fifth set in 2010. But Djokovic's comeback effort was more dramatic in 2011.

    Djokovic had rallied after losing the first two sets to force a fifth set. But after breaking Djokovic in the eighth game, Federer was serving for the match at 5-3 and had a double match point at 40-15.

    That's when Djokovic unleashed a crosscourt forehand return winner to save the first match point. John McEnroe described it as "one of the all-time great shots," according to The Guardian.

    Djokovic saved the second match point as well, and went on to win four straight games to close out the match.


8. Martina Navratilova vs. Steffi Graf, 1991 Semifinals

3 of 10

    Martina Navratilova was 34 years old and had lost four straight matches to Steffi Graf when the two met in the 1991 US Open semifinals.

    The 22-year-old Graf—who had beaten Navratilova in the 1988 and 1989 Wimbledon finals as well as the 1989 US Open finals—was the No. 1 seed at the 1991 Open, while Navratilova was seeded only No. 6.

    But Navratilova was the one who came through on the big points, claiming a 7-6 (7-2), 6-7 (6-8), 6-4 victory. She fought off four set points in the second set before Graf won the second-set tiebreaker on her fifth set point to even the match.

    Navratilova rebounded in the third set to take a 4-1 lead. But she double faulted twice in the sixth game to lose her serve, helping Graf to close to within 4-3.

    Graf held two break points with Navratilova serving for the match at 5-4. But she aced Graf to save the first break point, then answered the second with three big serves to close out the match.

    "I just didn't lie down and die the way I used to," Navratilova said, according to the Los Angeles Times. "This time, I hung in there."

7. Bjorn Borg vs. Jimmy Connors, 1976 Finals

4 of 10

    Jimmy Connors was ranked No. 1 but had not won a Grand Slam event since his one-sided victory over Ken Rosewall in the 1974 US Open finals, which was played on grass.

    The 1976 Open was played on gray-green Har-Tru clay. Borg had already won the premier clay-court tournament, the French Open—in 1974 and 1975—and had captured the first of his five straight Wimbledon titles two months earlier.

    However, Connors had beaten the Swede five times in a row heading into the 1976 Open finals. Connors' hard flat ground strokes and aggressive forays to the net always seemed to wear down the consistent Borg and his looping top-spin groundstrokes. Borg matched Connors shot for shot this time.

    “Some of the shots that Borg and I played that day, he with his little wood racket and me with my [Wilson] T-2000, were just flat-out crazy," Connors wrote in his book The Outsider, according to a Tennis Channel article by Steve Flink. "The crowd responded with the kind of passion that showed their appreciation for fierce competitors and great tennis.”

    The third set made this match special, and proved to be the turning point.

    After the players had split the first two sets, Connors led that third set 4-2 and was serving at 40-0, one point from assuming a commanding 5-2 lead. Borg won five straight points to take the game and later held a double set point at 6-4 of the tiebreaker.

    Connors hit two winners to even the tiebreaker, let a set point of his own slip away at 7-6, then saved two more set points against him at 8-7 and 9-8. After the latter point tied the tiebreaker 9-9, Borg was set to serve again, when a ball boy came running in from the back fence to tell the umpire the players needed to change sides again, according to Tennis.com.

    Amid the intensity of the match, both players and the umpire had forgotten it was time to change ends. Connors won the next two points to take the tiebreaker 11-9 after fighting off four set points.

    He had his first match point while serving at 5-4 in the fourth. Borg saved that with a difficult forehand passing shot and saved another before Connors finally finished off his 6-4, 3-6, 7-6 (11-9), 6-4 victory.

6. Jimmy Connors vs. John McEnroe, 1980 Semifinals

5 of 10

    Jimmy Connors and John McEnroe never liked each other, and both were American stars with an attitude, as noted in The National.

    That dynamic and McEnroe's tirades against the chair umpire that day added spice to a 1980 US Open semifinal that had plenty of twists and turns. McEnroe won the match 6-4, 5-7, 0-6, 6-3, 7-6 (7-3) but not before a lot of entertainment had taken place.

    McEnroe led 6-4, 5-4, when Connors suddenly took control in one of his trademark runs. Connors won 11 straight games and found himself leading two sets to one and 2-0 in the fourth set after winning the third at love.

    It was during that third set that McEnroe exploded on the chair umpire, calling him Mr. Incompetent among other things. Connors refused to give McEnroe the spotlight during the outburst, strategically placing himself on the wall to sit out the argument.

    McEnroe righted himself to win the fourth set and was serving for the match at 5-4 in the fifth. But Connors responded with two big groundstroke winners to break McEnroe's serve and tie the match.

    It was during that fifth set that McEnroe lost control of his racket. It flew the length of the court, barely missing Connors and costing McEnroe a $250 fine, according to Sports Illustrated. Ultimately they went to a fifth-set tiebreaker, at which point Connors' game deserted him. Serving at 1-2, Connors made two bad errors to give McEnroe an insurmountable 4-1 lead.

    "The two worst points of my life," Connors said, according to Sports Illustrated.

    McEnroe went on to beat Bjorn Borg in the finals in another classic.


5. Venus Williams vs. Serena Williiams, 2008 Quarterfinals

6 of 10

    Serena and Venus Williams had each won eight of their previous 16 sisterly meetings when they met in the 2008 US Open quarterfinals. This was probably the most engaging of their 24 matches, not only for the caliber of the tennis but because of Serena's comebacks in both sets.

    While looking ahead to the semifinals after Serena's 7-6 (8-6), 7-6 (9-7) victory, the Associated Press account provided the following assessment:

    It's tough to imagine that either of those contests could come close to producing the quality or competition managed Wednesday by a couple sisters who grew up honing their strokes on the same court in Compton, Calif. Both played brilliantly. Venus smacked serves at up to 125 mph, Serena at up to 115 mph. They somehow returned those. They hit groundstrokes and volleys that would be the envy of nearly every other woman on tour. They chased down balls with "You thought that was a winner?!" defense.

    Venus had beaten Serena in the finals of Wimbledon two months earlier to give each sister five wins in their 10 Grand Slam event matchups. And Venus held the upper hand in much of their 2008 US Open clash.

    The No. 7-seeded Venus led 5-3 in the first set, but the No. 4-seeded Serena battled back to force a tiebreaker. Serena then fought off a double set point against her at 6-4 of the breaker to capture the first set.

    Venus held a 5-2 lead in the second set, and had a triple set point at 5-3, 40-0. Serena saved all three of those as well as another set point at 6-5. Venus had another triple set point while leading 6-3 in the tiebreaker, but again Serena refused to go away.

    Serena saved all three of those set points and won the second-set tiebreaker 9-7. Serena had saved 10 set points in all, including two triple-set-point situations in the second set.

    "I felt like I was always in control," Venus said afterward, according to Associated Press. "If it was someone else, I definitely feel like I would have won the match."

    Serena went on to win the title.

4. John McEnroe vs. Bjorn Borg, 1980 Finals

7 of 10

    The 1980 US Open finals was in many ways simply a continuation of the epic match Bjorn Borg and John McEnroe had played two months earlier at Wimbledon.

    McEnroe's 7-6, 6-1, 6-7, 5-7, 6-4 victory in the Open did not quite reach the heights of their Wimbledon encounter, which included the unforgettable 18-16, fourth-set tiebreaker. But it borrowed much of the intrigue from that earlier match.

    It was still a clash of the top two players, with their very different styles and personalities providing polar opposites on the court.

    As Sports Illustrated put it:

    However many more tennis matches Bjorn Borg and John McEnroe are fated to play against each other, surely their names will be linked forever by the memories from a single summer. The summer of 1980. The summer of the tennis bookends. The summer that Borg started by defeating McEnroe in a glorious final at Wimbledon on July 5 and that McEnroe ended by checkmating Borg right back in a glorious final at New York's Flushing Meadow on Sunday.

    The resiliency of Borg was on display in the third set. He appeared to be out of the match after offering little resistance in the second set. But Borg roared back, hitting five clean winners to take the third-set tiebreaker, then won the fourth set to tie the match.

    It was Borg who seemed to be in control at that point. He was almost invincible in that situation, having won 13 straight matches that went five sets. Plus McEnroe had played a marathon five-setter while beating Jimmy Connors in the semifinals and had to be running out of gas.

    But McEnroe held firm, breaking Borg in the seventh game of the deciding set with the help of two Borg double faults and McEnroe's strong cross-court backhand on break point. McEnroe then served out the match for his second straight U.S. Open title.

    "The level of play, the intensity, was higher at Wimbledon," Borg said afterward, according to Sports Illustrated. "We both can play better. You will see the best matches, the best tennis, from us in the future."

    But the drama involved when Borg met McEnroe in the finals of a Grand Slam event was always at a high level.

3. Steffi Graf vs. Monica Seles, 1995 Finals

8 of 10

    The buildup to the 1995 US Open finals was as much a part of the story as the drama involved in Steffi Graf's 7-6, 0-6, 6-3 victory over Monica Seles.

    Seles was playing in just her second tournament after a 2 1/2-year absence. She had been sidelined since April 1993, when she was stabbed in Hamburg by a fan who wanted Graf, a German, to regain supremacy over Seles, who was the No. 1 player at the time.

    Graf spent much of the 1995 US Open ducking the German press, who wanted her reaction to the fact that her father, Peter, was currently in jail in Germany for failure to pay income tax on more than $1.5 million on his daughter's earnings, according to the Sports Illustrated report.

    The night before the finals, Graf had spent time at a New York hospital having an MRI performed on her aching foot. The match provided its own intrigue, so much, perhaps, that reliable Sports Illustrated had the third-set score wrong in its report.

    Seles thought she had won the first set on an ace at 6-5 in the tie-breaker. But the ball was called out, and Graf hit a winner on the second serve to save the set point.

    Graf ultimately won that tiebreaker, but Seles dominated the second set, winning it at love in just 27 minutes. The momentum seemed to be all on Seles' side, but Graf responded with some of her best tennis in the third set.

    With Graf serving at 5-3, 40-15 of the deciding set, Seles hit a crushing forehand winner on a service return to stay alive. But she erred on Graf's second match point to end it.

    "This is the biggest win I have ever achieved," Graf said, according to SI, after getting her 18th Grand Slam title. "There is nothing that even comes close to this one."

2. Chris Evert vs. Martina Navratilova, 1984 Finals

9 of 10

    Of the 80 matches in the Chris Evert-Martina Navratilova rivalry, Navratilova's 4-6, 6-4, 6-4 victory in the 1984 US Open may have been the most compelling.

    Navratilova had beaten Evert 12 straight times coming into that match and most of the results were one-sided. Navratilova had beaten Evert 6-3, 6-1 in the U.S. Open finals the previous year and had defeated Evert 6-1, 6-3 on Evert's best surface in the finals of the 1984 French Open.

    More of the same was expected in the 1984 US Open finals. Instead, the match became a turning point.

    Evert did not win, but she showed more variety in her game and greater stamina. More significantly, at age 29, she showed herself and the world she could still compete with Navratilova. Evert beat Navratilova the next time they met, and the two competed on relatively even terms over the next four years.

    The 1984 US Open finals represented the 61st meeting between the two rivals, whose contrasting styles and friendship made all their matchups intriguing. For this one, Navratilova was riding a 54-match winning streak, one shy of Evert's Open Era record.

    When Evert broke through to win the first set, the crowd erupted. 

    It was "louder than anything I have ever experienced in my life," Evert said in an excerpt from Johnette Howard's book, The Rivals. "I remember walking off for the changeover thinking, 'I am finally going to do it.' And it seemed like everyone else thought so too."

    Evert might have won her seventh US Open title if she had taken advantage of an opportunity in the 10th game of the second set. She trailed 5-4, but hit three marvelous winners to get a double break point at 15-40 on Navratilova's serve.

    Even though Navratilova missed her first serve on the next two points, Evert was unable to produce the big shot. Navratilova held serve to win the second set, then finished it off in the third. Despite the brilliant shot-making by both players, Evert felt she choked.

    "It was the most devastated I've ever felt over a tennis match," she said in The Rivals.

    Navratilova's winning streak would reach 74 before she lost to Helena Sukova in the Australian Open.

1. Andre Agassi vs. Pete Sampras, 2001 Quarterfinals

10 of 10

    Even though it was not a finals, the 2001 US Open quarterfinals between Andre Agassi and Pete Sampras featured everything a tennis fan could want.

    Two established American stars who already owned 21 Grand Slam singles titles between them met for the 32nd time in their careers. They had already developed a riveting rivalry with their contrasting styles and personalities.

    Sampras held a slim 17-14 lead in match victories, including victories in the 1990 and 1995 US Open finals. The drama and shot-making were accentuated by the US Open's night-session crowd, known for its loud involvement in matches. Those New York crowds adore sentimental favorites, a role Agassi, at age 31, and Sampras, at 30, both filled.

    The contest was close throughout. In fact, there was not a single service break in the match.

    "Probably about as good as it gets, playing the very best in a night match at the US Open," Sampras said after the match, per the Associated Press. "The atmosphere was phenomenal, and it was so close."

    When Sampras finished off his 6-7 (7-9), 7-6 (7-2), 7-6 (7-2), 7-6 (7-5) victory at 12:14 a.m. virtually everyone in the announced crowd of 23,033 at Arthur Ashe Stadium was still in attendance.

    Agassi fought off a triple set point in the first-set tiebreaker, coming back from 6-3 deficit to claim it 9-7. Sampras won the second-set tiebreaker on a deft drop volley, then finished off the third-set tiebreaker with consecutive aces.

    Sampras hit two more aces in the fourth-set tiebreaker and had a triple match point at 6-3. However, the suspense increased when Sampras double faulted and missed a volley to make it 6-5. But Agassi missed a short forehand on the third match point, giving Sampras the match.