The Most Shocking Upsets in Wimbledon History

Jake CurtisFeatured ColumnistJune 26, 2013

The Most Shocking Upsets in Wimbledon History

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    Rafael Nadal's stunning straight-sets loss to Steve Darcis in the first round on Monday raises an obvious question: Was that the biggest upset in Wimbledon history? And what about the second-round losses by Roger Federer and Maria Sharapova?

    All three are certainly in the discussion.

    Gauging the magnitude of an upset is a subjective exercise, of course.

    Even time can affect the status of an upset. When unseeded 18-year-old Billie Jean Moffitt stunned top-seeded Margaret Smith in Smith's opening match of the 1962 Wimbledon tournament, it seemed like a major upset. In retrospect, the result doesn't seem as surprising because Moffitt, who became Billie Jean King, went on to win six Wimbledon singles titles.

    The bottom line in the determination is this: How shocked were tennis fans by the result?

    This proposed list of 15 shocking Wimbledon results was quickly expanded by two with the losses by Federer and Sharapova. So here's a countdown of the 17 most stunning upsets in Wimbledon history.

17. Charlie Pasarell over Manuel Santana, 1st Round, 1967

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    Charlie Pasarell's 10-8, 6-3, 2-6, 8-6 victory over Manuel Santana made the list for one important reason: It was the first time that a defending champion and No. 1 seed had lost in the first round at Wimbledon.

    Pasarell was no slouch. He was the top-ranked American and had beaten Santana once out of their only two previous meetings before their 1967 Wimbledon matchup, according to an Associated Press report.

    However, he had not had much success at Wimbledon, never getting past the third round in his four previous attempts. It left him unseeded in 1967.

    But this attempt was different.

    "This is the first time I've had an opportunity to come in advance of Wimbledon and practice on grass," Pasarell said after beating Santana, according to Canadian Press.

16. Arthur Ashe over Jimmy Connors, Finals, 1975

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    Although Arthur Ashe's 6-1, 6-1, 5-7, 6-4 victory over Jimmy Connors in the 1975 finals may not have been as surprising as other upsets on this list, it deserves a spot because of the significance of the match and the attention it received.

    Connors was an overwhelming 3-to-20 betting favorite against Ashe, according to an ESPN article. In fact, he was a 9-to-10 favorite to win in straight sets.  

    Ashe, then 31, was in the Wimbledon final for the first time, making it as the No. 6 seed following a five-set victory over Tony Roche in the semifinals. The top-seeded 22-year-old Connors had not lost a set en route to the final and had lost only six games while beating Ken Rosewall in the 1974 Wimbledon final.

    But against Connors, Ashe took the pace off his shots, relying on angles and finesse to frustrate Connors' powerful groundstrokes.

    The shock value of the victory and the way it was achieved resonated for weeks.

15. Michelle Larcher de Brito over Maria Sharapova, 2nd Round, 2013

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    Maria Sharapova was having an outstanding 2013 season before her surprising 6-3, 6-4 second-round loss to Michelle Larcher de Brito, the world's No. 131 player.

    Since her loss in the Australian Open semifinals, Sharapova had lost to only one player on the court, Serena Williams. Sharapova had reached the finals of the last five tournaments she had completed and won two of them. Williams beat her in all three of the others.

    Sharapova has not had great success on the grass at Wimbledon, but she won the event in 2004 and was a finalist in 2011.

    Sharapova certainly figured to beat de Brito, who had won only two tournament matches all year, both against players ranked outside the top 200. De Brito had lost in qualifying to a player ranked 229th at the grass-court tuneup in Nottingham, England two weeks ago, and her only Wimbledon victory before this year came against qualifier Klara Zakopalova in 2009.

    An injury to her hip seemed to hamper Sharapova's movement in the loss, according to USA Today. That is certainly a mitigating factor in the upset, but it is not enough to prevent its inclusion on this list.

14. Ian Collins over Henri Cochet, 1st Round, 1932

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    By the time he faced Ian Collins in the first round of the 1932 Wimbledon tournament, Henri Cochet had won seven Grand Slam singles titles, including the 1927 and 1929 Wimbledon crowns.

    Cochet had won the French Championship just two weeks earlier, and, as the No. 1 seed at Wimbledon in 1932, he was the favorite to win a third title at the All England Club, especially since Bill Tilden and Rene Lacoste were not competing.

    Collins was a 29-year-old Scotsman who would never get as far as the quarterfinals of a Grand Slam singles event. Much of his limited success came in doubles.

    But on June 21, 1932, he stunned the heavily favored Cochet  6-2, 8-6, 0-6, 6-3 at the All England Club.  According to a report in the Sydney Morning Herald, Cochet got so frustrated during the match that he had a linesman removed.

    As Time noted, people had just assumed Cochet would be a finalist at Wimbledon that year before his stunning loss to Collins.

    Cochet's first-round loss to Nigel Sharpe a year earlier was a major upset as well. But Cochet was still feeling the effects of the flu in that 1931 Wimbledon loss, according to the Brisbane Courier.

    He had no such excuse against Collins.

13. Lori McNeil over Steffi Graf, 1st Round, 1994

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    Lori McNeil became the first woman in history to beat a defending Wimbledon champion in the first round when she knocked off No. 1 Steffi Graf 7-5, 7-6 in 1994.

    Not only had Graf won the title in 1993, but she had won five of the previous six Wimbledon crowns, including the last three in a row. She had won 21 straight matches at Wimbledon when she faced McNeil.

    McNeil was 30 years old, six years past her career-high ranking of No. 9 and eight years past her previous best showing in a Grand Slam event when she got to the semifinals of the 1986 U.S. Open.

    McNeil had left the tour for six weeks in 1994 starting in late March to deal with the grief of losing her father, who had committed suicide in January. She had lost 6-0, 6-0 to Mary Pierce in the third round of the French Open.

    However, at Wimbledon, Graf could not handle the strong serve-and-volley game of the unseeded McNeil, as described by Sports Illustrated.

    McNeil's victory might have been higher on this list had it not been for the fact that McNeil had beaten Graf the last time they met, at the Virginia Slims championships in 1992.  Plus McNeil was ranked 22nd at the time, so Graf knew it would be a challenge.

12. Nick Brown over Goran Ivanisevic, 2nd Round, 1991

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    Goran Ivanisevic's big serve and high-risk game gave him a chance to fare well at Wimbledon, as he proved while getting to the finals in 1992, 1994 and 1998 and winning it in 2001.

    But it also made him erratic and susceptible to inexplicable losses, such as his second-round loss to Nick Brown in 1991, one year after Ivanisevic had reached the Wimbledon semifinals.

    Ivanisevic was seeded 10th at Wimbledon in 1991, and, as noted by the Chicago Tribune, his style and experience gave him a chance to win the tournament.

    The 30-year-old Brown, meanwhile, was ranked 591st and had quit tennis in 1984 before returning in 1989. He had played just three tournaments in 1991 coming into Wimbledon, and one of those was a Challenger event. He had lost in the first round of all three, including a 6-4, 6-1 defeat at the hands of Felix Barrientos, who was ranked 249th at the time.

    An Englishman, Brown got a wild-card entry into Wimbledon, and he beat 174th-ranked Mark Keil in the first round to set up a second-round match against Ivanisevic.

    He stunned Ivanisevic 4-6, 6-3, 7-6 (7-3), 6-3.

    "I play one of worst matches in my life," Ivanisevic said, according to the Philadelphia Inquirer.  "I was too slow, moving badly, and I am missing easy volleys. He did nothing."

    Brown lost to 90th-ranked Thierry Champion in the third round. He then lost to 230th-ranked Peter Nyborg in a Challenger event in his only subsequent tournament.

11. Sergiy Stakhovsky over Roger Federer, 2nd Round, 2013

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    Roger Federer won Wimbledon last year and was ranked the best player in history by the Tennis Channel in 2012.  Based on that alone, his 6-7, 7-6, 7-5, 7-6, second-round loss to 116th-ranked Sergiy Stakhovsky this year deserves a spot on the list.

    Federer has 17 Grand Slam titles to his name, the most in history.  More significant is the fact that he had reached at least the quarterfinals in 36 straight Grand Slam events before this loss.

    Having that remarkable run of consistent excellence broken by a player who's done nothing notable makes it a shock.

    There's no question Federer, who turns 32 in two months, has struggled this year, at least by his standards.  

    He had reached the finals of only two of his eight 2013 tournaments coming into Wimbledon and has claimed only one title. He lost in the quarterfinals at the French Open to Jo-Wilfried Tsonga in straight sets, and he has not beaten a top-10 player since January.

    But he remains a threat on grass, as evidenced by his seven Wimbledon titles, including one just last year.

    Furthermore,  Stakhovsky had won just two main tour matches since February before Wimbledon, and he had not beaten a top-50 player this year.

    In six previous appearances at Wimbledon, including two failed qualifying attempts, Stakhovsky had won just one match, that coming in 2011 against 273rd-ranked Daniel Cox.

    However, this is the fourth time since 2009 that Stakhovsky has reached the third round of a Grand Slam event, and he beat No. 19-ranked Alexandr Dolgopolov in the 2012 French Open. That and Federer's recent struggles prevent this upset from being rated higher.

10. Roger Taylor over Rod Laver, 4th Round, 1970

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    Rod Laver virtually owned the All England Club in the 1960s. He did not lose a match at Wimbledon from 1961 through 1969, winning the event in 1961, 1962, 1968 and 1969. (He was barred from the event in the five years between 1963 and 1967 because he was a professional.)

    When he faced Roger Taylor in the fourth round in 1970, Laver had won 31 consecutive matches at Wimbledon, and his only losses there since 1958 had come in the finals in 1959 and 1960 at ages 20 and 21.

    Although he would not win a major in 1970, Laver would go a combined 8-0 that year against Wimbledon champion John Newcombe and U.S. Open champ Ken Rosewall.

    The 1970 Wimbledon was Laver's first major since he completed the Grand Slam in 1969 by winning the U.S. Open. He was seeded first at Wimbledon again and was already a legend, having won 11 major titles despite his enforced five-year absence from Grand Slam events.

    Taylor was seeded 16th in the 1970 Wimbledon. He had been a semifinalist in 1967 but had lost in the second round the next two years.

    He was not given much of a chance in the fourth round against Laver, who was ranked the second-best player in history by the Tennis Channel in 2012.

    But Laver was merely the second-best player on the court on June 27, 1970. Taylor, a 28-year-old Englishman spurred by the Wimbledon crowd, beat Laver 4-6, 6-4, 6-2, 6-1, with Laver double-faulting on the final point.

9. Andrei Olhovskiy over Jim Courier, 3rd Round, 1992

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    Heading into the 1992 Wimbledon tournament, Andrei Olhovskiy had lost in the first round of eight straight tournaments and was riding a nine-match losing streak. The last time he had won a main draw match was in a Challenger event in January, and his ranking had fallen to No. 193.

    He had to qualify to make the main draw at Wimbledon and managed to get past two players ranked outside the top 100 to reach the third round. There he'd face Jim Courier, the world's top-ranked player, who was riding a 25-match winning streak and had won the first two legs of the Grand Slam: the Australian Open and the recent French Open.

    Even though grass was not Courier's best surface, this was clearly a mismatch for other reasons.

    But what seemed impossible happened. Olhovskiy beat Courier 6-4, 4-6, 6-4, 6-4, becoming the first qualifier to beat a top seed at Wimbledon since the Open era began in 1968.

    It also ended Courier's run of four straight tournament titles and his chance at a Grand Slam.

    So, Andrei, how did you do it?

    "I don't know," he said, according to the Los Angeles Times.

8. Eleni Daniilidou over Justine Henin, 1st Round, 2005

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    Justine Henin's 7-6, 2-6, 7-5 first-round loss to 76th-ranked Eleni Daniilidou was eerily similar to Rafael Nadal's loss to Stephen Darcis.

    Like Nadal this year, Henin was coming off a victory in the French Open. And, like Nadal, she was struggling with a leg injury that prevented her from playing the grass-court warm-up events preceding Wimbledon.

    Nonetheless, this was still a major surprise.

    Henin had been ranked No. 1 in 2003 and would reach the top spot again in 2006. She had reached at least the semifinals each of the past three times she participated at Wimbledon. More significantly, Henin had won 17 straight matches coming into the 2005 Wimbledon.

    Meanwhile, Daniilidou had lost in the first round of six of her 2005 tournaments heading into Wimbledon. That included a first-round loss in the French Open to qualifier Sofia Arvidsson. Daniilidou was beaten in the first round of the 2004 Wimbledon by unseeded Magui Serna.

    But she had her day in the sun in 2005 against Henin, who knew Daniilidou would be a challenge on grass.

    "This was the worst draw I could have got," Henin said, according to the Daily Telegraph

    Adding to the degree of difficulty for Daniilidou was a calf injury she suffered in the third set that required the attention of a trainer, according to the Daily Mail. Daniilidou, 22, persevered for the biggest win of her career. 

7. George Bastl over Pete Sampras, 2nd Round, 2002

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    Although Pete Sampras' run of seven Wimbledon titles in eight years had been halted by Roger Federer in an epic five-set fourth-round match in 2001, Sampras was still seen as a Wimbledon contender in 2002.

    Sampras was seeded sixth in 2002 and had blown by Martin Lee in straight sets in the first round. He was expected to do the same in the second round against George Bastl, a Swiss player ranked 145th.

    Bastl had not won a single main tour match in 2002 coming into Wimbledon, having played mostly Challenger events. In fact, his victory over 152nd-ranked Denis Golovanov in the first round at Wimbledon and a subsequent victory over 233rd-ranked Julio Silva in Brazil were his only main tour victories of the year besides his upset of Sampras.

    Bastl was fortunate to be in the 2002 Wimbledon tournament at all.  He had lost in qualifying, but he got a berth in the main draw as a lucky loser after Felix Mantilla withdrew with an ankle injury.

    And somehow he beat Sampras 6-3, 6-2, 4-6, 3-6, 6-4.

    Afterward, BBC commentator John Lloyd said "That is the worse grass-court match I have seen Pete Sampras play. It is a staggering result, one of the biggest shocks in Wimbledon history."

    Bastl would never win another Wimbledon match. He lost to David Nalbandian 6-2, 6-2, 6-2 in the third round in 2002, then lost to players ranked outside the top 250 in his subsequent three appearances at Wimbledon, the latter two losses coming in qualifying.

6. Peter Doohan over Boris Becker, 2nd Round, 1987

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    Boris Becker was just 19 years old when he faced 70th-ranked Peter Doohan in the second round of the 1987 Wimbledon. But Becker had already won Wimbledon the previous two years and was the No. 1 seed at Wimbledon for the first time. He was still improving.

    Two weeks earlier, Becker had won the grass-court warm-up event at Queen's Club, beating Jimmy Connors in the finals. Becker's first-round victim at Queen's Club was Doohan, who had gone down rather routinely in straight sets.

    Doohan, meanwhile, came into Wimbledon having lost his opening match of both of his grass-court tune-ups, losing to Becker, then falling to 246th-ranked Paul Chamberlin the week before Wimbledon.

    More telling was that Doohan had lost in the first round of all four Wimbledons he had played before the 1987 event at the All England Club.

    Tendinitis of the right shoulder had limited Doohan to seven singles matches the previous year, and he lost all seven. There was no reason to believe Doohan would provide a challenge for Becker at an event the German had owned.

    However, Doohan pulled off the shocker, beating Becker 7-6, 4-6, 6-2, 6-4.

    "I have to prove to everybody this is not a once-in-a-lifetime thing, that they would never hear from Peter Doohan again," the 26-year-old Doohan said afterward, according to the New York Times. "I don't blame them for thinking that way.''

    Doohan beat 166th-ranked Leif Shiras in the next round at Wimbledon, then won only one more Grand Slam singles match the rest of his career. That lone win came against 233rd-ranked Steven Guy in the 1988 Australian Open.

5. Lukas Rosol over Rafael Nadal, 2nd Round, 2012

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    Rafael Nadal's 6-7 (9-11), 6-4, 6-4, 2-6, 6-4, second-round loss to Lukas Rosol in 2012 was Nadal's last tournament match for more than seven months. But the knee problem that caused that layoff can't completely explain a result this surprising.

    Nadal was No. 2 in the world at the time. He was a finalist at the 2012 Australian Open and won the 2012 French Open. Plus he had beaten top-ranked Novak Djokovic three times over the previous two months.

    Nadal had become a skilled grass-court player, getting to the Wimbledon finals each of the five previous times he'd participated and winning it twice, in 2008 and 2010.

    On the other hand, Rosol was ranked 100th and had lost in the first round in eight of his 2012 tournaments heading into Wimbledon. He had lost 6-0, 6-0, 6-2 to 63rd-ranked Philipp Petzschner at the Australian Open earlier in the year.

    Rosol had never played in the Wimbledon main draw, losing in the first round of qualifying in all five of his previous attempts. Even though he didn't have to qualify for Wimbledon this time, his prospects didn't look much better, as he had failed to qualify for the grass-court tune-up at Eastbourne, England the previous week.

    None of that mattered in the second round.  Rosol let three set points slip away in a first-set tiebreaker against Nadal, so any chance he had of putting some early pressure on the favorite seemed to disappear. Surprisingly, though, Rosol dominated the rest of the match, playing spectacular tennis in the final set.

    Nadal spent much of the match complaining and looking frustrated. He even bumped into Rosol during a change-over in the third set. Rosol did not think it was an accident.

    "He wanted to take my concentration... I knew that he will try something," said Rosol, according to the Associated Press.

    Intentional or not, the bump did not prevent a shocking upset.

4. Jelena Dokic over Martina Hingis, 1st Round, 1999

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    Martina Hingis suffered two inexplicable losses at Wimbledon. The first-round loss to Virginia Ruano Pascual in 2001 was stunning, but not as shocking as her loss to 16-year-old Jelena Dokic in the opening round two years earlier.

    Hingis had won Wimbledon in 1997 and was a semifinalist in 1998. And she was still improving. She entered the 1999 Wimbledon ranked No. 1 in the world just a few months shy of her 19th birthday.

    She was coming off a three-set loss to Steffi Graf in the finals of the French Open and had won the other major that year, the Australian Open. In the latter she had beaten Dokic 6-1, 6-2 in the third round after Dokic, an Australian, had received a wild-card entry.

    Dokic was lauded as a top-flight junior with potential, and she had shown some promise early in the year. However, she had lost to 216th-ranked Emmanuelle Curutchet in the first round of the French Open less than three weeks after losing to 145th-ranked Ines Gorrochategui in Poland.

    Dokic, ranked 129th, was playing Wimbledon for the first time in 1999, and she had to win three qualifying matches just to get into the main draw to face Hingis.

    What happened against Hingis was almost beyond belief. Not only did Dokic beat Hingis, but she crushed her 6-2, 6-0, reeling off the final 11 games to complete the upset in just 54 minutes.

3. Ivo Karlovic over Lleyton Hewitt, 1st Round, 2003

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    Lleyton Hewitt became the first defending Wimbledon champion in the Open Era (since 1968) to lose in the first round when he lost to Ivo Karlovic 1-6, 7-6, 6-3, 6-4 in 2003.

    But it wasn't just the historic nature of the loss that made it so shocking. The 6'10" Karlovic had won only two main tour matches in his entire career before meeting Hewitt, according to the Associated Press. He was ranked 203rd and had failed to qualify for a Grand Slam event in 10 previous attempts, 

    "I'd never seen him play," said Hewitt afterward, according to the Associated Press. "I'd seen him walk around a bit."

    Hewitt was the top seed at Wimbledon, and his world ranking had slipped from No. 1 to No. 2 just two weeks earlier. He had failed to get past the quarterfinals in any tournament since March, but Karlovic seemed like an easy touch. After all, Karlovic had qualified for only one main tour event in 2013, losing in the second round at Queens Club two weeks earlier

    Hewitt breezed through the first set against Karlovic in just 19 minutes as expected. But then everything went wrong for Hewitt and right for Karlovic, who served 18 aces to help pull off the shocker.

2. Doug Flach over Andre Agassi, 1st Round, 1996

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    Grass was never Andre Agassi's best surface, but he had won his first Grand Slam title by taking the 1992 Wimbledon crown, and he had reached the semifinals in 1995 before losing to Boris Becker.

    Seeded No. 3 seed in the 1996 Wimbledon after being ranked No. 1 just four months earlier, Agassi certainly was not expected to lose his opener to Doug Flach, a qualifier ranked 281st. Agassi had beaten Flach in straight sets in their only two career encounters to that point.

    In his only previous Wimbledon match, Flach had lost in the first round in 1995 to Guy Forget, then ranked 1,130th, 6-1, 6-2, 6-2.  More significantly, the match against Agassi was Flach's first main tour match in more than a year, as his ranking had slipped to No. 641 by the end of 1995.

    Flach's 2-6, 7-6, 6-4, 7-6 upset of Agassi was Flach's first main tour match victory in more than two years.

    The magnitude of Flach's upset was evident in his post-match quotes, as recorded by the Baltimore Sun:

    I'm so excited, as excited as anyone could be at this moment. This is the highlight of my career. The biggest moment. Last month I was playing in satellite tournaments just to get my ranking up high enough so I could play in the qualifiers here. In January my ranking was 600.

1. Steve Darcis over Rafael Nadal, 1st Round, 2013

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    People are still searching for reasons to explain Steve Darcis' 7-6, 7-6, 6-4 first-round upset of No. 5 seeded Rafael Nadal this year.

    Certainly, the knee injury that affected Nadal's movement and prevented him from playing a grass-court warm-up event was a factors.

    However, if we look at the cold, hard facts, it's difficult to grasp how it happened.

    First of all, Nadal's No. 5 seeding was misleading, the result of a computer ranking that penalized him for having missed seven months of action before his return last February.

    His remarkable 2013 results heading into Wimbledon stated rather clearly that he was the best player in the world at the moment.

    He had played nine 2013 events, got to the finals in all of them and won seven. Nadal's only loss since early February came against No. 1-ranked Novak Djokovic in April, and Nadal was riding a 22-match winning streak.

    Nadal was coming off a victory in the French Open where he captured his 12th Grand Slam crown. Two of those major titles came in 2008 and 2010 at Wimbledon, where Nadal had been a finalist in five straight appearances (he did not play the event in 2009) before his second-round loss to Lukas Rosol in 2012 when he was injured.

    Few had even heard of Darcis, and it's not surprising.

    His only two match victories in 2013 came in a Davis Cup match against Nenad Zimonjic, who was unranked at the time and has since improved to 1,326th, and in France against 166th-ranked Adrian Mannarino. Darcis had not won a match in the main draw of a tour event since the first week of February, and he was ranked 135th heading into Wimbledon.

    Darcis had won just one Wimbledon match in four previous tries, and last year he lost in the first round to Guillaume Rufin, who was ranked 168th.

    The only evidence that Darcis might challenge Nadal was Darcis' victory over Tomas Berdych in the 2012 Olympics played at Wimbledon.

    But no one expected Darcis to beat Nadal, certainly not in straight sets. The headline in the Daily Telegraph sports section the next day read, "Shock of the Century."

    Not only did Darcis stun Nadal, but it turns out that Darcis did it with an injured shoulder. The Daily Telegraph reported that Darcis had to withdraw before his second-round match because of a shoulder problem he sustained against Nadal.