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London 2012: The 12 Most Unforgettable Matches in Olympic Tennis History

David ReplogleContributor IIIJanuary 5, 2017

London 2012: The 12 Most Unforgettable Matches in Olympic Tennis History

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    When tennis made its return to the Olympic stage in 1988 after a 64-year absence, the sport was greeted with appropriate skepticism.

    Why was Steffi Graf—owner of all four Grand Slams played that year— stomping around Seoul? Chris Evert, Stefan Edberg, Gabriela Sabatini—these were not just professionals, but seasoned, glorified professionals at that. 

    Since the inception of the American basketball "Dream Team" in '92, however, the professional vs. non-pro discussion has largely fallen off the radar.

    The debate still rages on about tennis' legitimacy in the Games (check out how Tennis.com's Steve Tignor and Pete Bodo argued both sides), but one thing is certain—the amount of surprising stunners and nail-biting thrillers that Olympic tennis has produced has been outstanding.

    London excluded (I figure there'll be a Top 12 or Top 10 list following the conclusion of the Games), here are the 12 greatest matches in Olympic history.

12: 2004 Athens 2R, Tomas Berdcyh (CZE) D. Roger Federer (SUI)

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    Berdych d. Federer 4-6 7-5 7-5

    Kicking off our countdown is one of the most shocking—and unforeseen—upsets in Olympic history.

    Nowadays, we know Tomas Berdych as the irascible, big-hitting bomber who's been a fixture in the Top 10 and the later rounds of Slams for a long while. But back in August 2004, he was a 79th-ranked upstart who'd yet to take down anyone close to Roger Federer's status.

    The Swiss maestro had put together a dream season to date—capturing the Australian Open and ascending to No. 1, defending his Wimbledon title—and had his sights set on a gold medal.

    But Berdych had other ideas. Even after dropping a tight first set, the Czech continued to put heavy pressure on Federer from the baseline. Using a strategy that many would come to adopt in the next decade—Rafael Nadal, most of all—Berdych pounded the Federer backhand 'til the bitter end.

    The world No. 1 capitulated 7-5 in the third, capping off a second straight disappointing Olympic Games—he lost the bronze medal match in 2000 in Sydney. 

11: 2000 Sydney F, Yevgeny Kafelnikov (RUS) D. Tommy Haas (GER)

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    Kafelnikov d. Haas 7-6(4) 3-6 6-2 4-6 6-3

    One beautiful aspect of Olympic tennis is that when national pride is on the line, big upsets are frequent (like the one I recounted in the previous slide).

    No event better illustrates this fact than the 2000 Sydney men's singles draw, which opened big time after the first two days of competition.

    Top seed Marat Safin, fresh off his U.S. Open triumph, fell in the first round. So did Lleyton Hewitt, Tim Henman, Marcelo Rios and Michael Chang. The exodus of seeds led to this final between two of the sport's second-tier stars.

    Second-tier or not, Yevgeny Kafelnikov and Tommy Haas joined forces to put on a great display of grit and passion. Pitting contrasting styles against one another—Kafelnikov's grueling baseline game and staying power vs. Haas' all-court game and natural athleticism—the two men battled for five sets and nearly four hours.

    In the end, Kafelnikov was just too consistent for his German foe. For a guy who rarely smiled on court—or showed any emotion, for that matter—you could see how much a gold medal mattered to the patriotic Russian.

    One of the game's consummate hard workers, he'd always been overshadowed in his career by more spectacular players like Sampras, Agassi and Kuerten—despite winning a couple of Grand Slams.

    But on this September evening in Sydney, it was truly his golden moment.

    The match can be seen in its epic entirety in the YouTube clip provided. 

10: 2004 Athens Doubles F, Gonzalez/Massu (CHI) D. Kiefer/Schuettler (GER)

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    Gonzalez/Massu d. Kiefer/Schuettler 6-2 4-6 3-6 7-6(7) 6-4

    Tennis at the 2004 Athens Olympics can be summed up in two words: "Chilean heroics."

    This No. 10 spot on the list is one of the most overlooked and jaw-dropping matches in doubles history, let alone Olympic history. Here's why:

    --Gonzalez teamed with Massu less than three hours after outdueling Taylor Dent in grueling fashion for the singles bronze (a victory that might just be reviewed later on down the line), a match which had taken about three and a half hours to complete. 
    --The Chileans saved four match points in the fourth set tiebreak and overcame a 3-1 deficit in the fifth set. They then needed three match points of their own to finish it out.
    --The match finished at 2:39 a.m.
    --Despite the late time of the match, the crowd was as electric as an Olympic event could hope for. 
    --Gonzalez and Massu had never captured an ATP tour doubles title together, let alone reach a doubles final.
    --Both winning men had played a ton of tennis. Massu, famously, was to play in the best-of-five gold medal final the following day.
    --Gonzalez was treated after the third set for hamstring and knee pain.
    --The quality of tennis was simply unbelievable. Watch the provided clip of the fourth set tiebreaker, which tells all.

9: 1996 Atlanta QF, Arantxa Sanchez-Vicario (ESP) D. Kimiko Date (JPN)

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    Sanchez-Vicario d. Date 4-6 6-3 10-8

    Drama. Grit. Competitive fire.

    Three components which made Arantxa Sanchez-Vicario's career so legendary, and so perfectly Spanish. 

    This memorable quarterfinal from the Atlanta Games showcases all three tenets of the "Barcelona bumblebee's" game exceptionally well, and also shows how demoralizing Sanchez-Vicario could be when she decided to sink her teeth into a match and, simply, never give up.

    The whole match can be found in parts on YouTube, but the clip I chose comes at the tail end of the match—we pick it up with Kimiko Date serving for the match at 8-7 in the third. That's when all hell breaks loose for the player from Japan.

    Suddenly, she can't keep a ball in the court. Her shots spray long and wide, her head hangs in dejection, her face gives way to more and more anguish. Before she knows it, she's lost the next three games in a flash—and any shot at a medal.

    Granted, it was a huge pressure situation. And it was a hot Georgian summer day. And Date wasn't particularly known for closing out big matches well. But more than anything, this match—and Date's sudden collapse—justifies exactly how demoralizing it could be to play Sanchez-Vicario.

    Looking across the net, Date saw the gleam in her opponent's eyes and the fiery fist pumps after each grueling point. And she knew that it just wasn't going to be her day, as so many other opponents had done in the past and would do in the future. 

    Sanchez-Vicario would go on to lose in the gold medal round to Lindsay Davenport, but not before cementing herself, yet again, as one of the game's most spectacular competitors. 

8: 2008 Beijing SF, Federer/Wawrinka (SUI) D. Bryan/Bryan (USA)

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    Federer/Wawrinka d. Bryan/Bryan 7-6(6) 6-4

    The Swiss No. 1's chances at a coveted singles gold ended against James Blake in the Beijing quarterfinals, but the Fed Express famously got to steamrolling in the doubles draw.

    Coming up against the doubles team of the decade, Federer and Stan Wawrinka tactic was to play "blitzkrieg dubs"—basically, belt the ball as fast as they could.

    Not a bad strategy (although it's a wonder the quartet made it out with all their body parts intact). By upping the pace—and the pace of play—the Swiss team robbed the Bryan brothers of a few of their uncanny abilities, like opening up the court and displaying deft hands at net.

    The quick shots and fast courts also resulted in a number of incredible rallies, most ending in mind-numbing winners. 

    The Swiss duo ended up winning the gold, lifting Federer from the doldrums after two heartbreaking back-to-back Slam losses and propelling him towards a 13th major at the U.S. Open that fall. 

7: 2004 Athens F, Nicolas Massu (CHI) D. Mardy Fish (USA)

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    Massu d. Fish 6-3 3-6 2-6 6-3 6-4

    His game—like that of most South Americans—was much more adept on slow red clay. And he certainly wasn't billed to make it into the medal rounds. But many forget that Nicolas Massu was ranked 14th and in the midst of the best season of his career when the Athens Olympics came about.

    The draw opened up nicely for players like Massu and Fish to make it through to the championship bout. Following Olympic men's tennis tradition, it seems, top seeds fell by the wayside early on.

    Berdych took out Federer. Marat Safin fell to Feliciano Lopez. Massu's compatriot Fernando Gonzalez beat Roddick in Round 3, before Fish disposed of him in the semis. Fish also took down fifth seed Juan Carlos Ferrero in the second round. 

    So a surprise medal winner was ripe for the picking. And despite Massu's higher ranking, many pundits picked Fish to take it. He'd proven himself in this tournament. He was a better hardcourt player. He was a better natural athlete, taller, faster—you name it. This was his gold to lose.

    Massu, though, perhaps fueled by the delirium of his five-set gold medal thriller in doubles just mere hours before this match, or pumped up by the raucous, energized crowd, didn't seem to agree that Fish was the favorite.

    The Chilean came out of the gates swinging, showing none of the nerves that Fish did in the opening set. When he found his back against the wall, down two sets to one, fighting fatigue and nerves, he kept getting better—or, as Fish put it, "more untired."

    It wasn't a glamorous matchup, or a glamorous match. The two players combined for 183 unforced errors, 15 double faults and 12 service breaks. Ultimately, though, it was a glorious, heroic, four-hour win for the unheralded Massu, who went from near-anonymity to having his name etched in the history books for all time with the gold medal.

    Fish, meanwhile, was crushed—and hasn't made it back to the Olympics since due to the mental scars this epic final left. 

6: 1992 Barcelona F, Jennifer Capriati (USA) D. Steffi Graf (GER)

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    Capriati d. Graf 3-6 6-3 6-4

    Prior to her explosive comeback run to the 2001 Australian Open championship, many thought this gold medal from the Barcelona Games would be what Jennifer Capriati would be most remembered for (on court, that is).

    Just 16 years of age, armed with lethal groundies and nothing to lose, Capriati entered the match with an 0-4 head-to-head record against the No. 2 ranked player and top seed at the Games.

    Graf, meanwhile, was the defending gold medal champion (she beat Gabriela Sabatini when tennis returned at those '88 Seoul Games) and had lost just 17 games in five rounds heading into the final. 

    Interestingly enough, Graf—who possessed arguably the steeliest nerve, men or women, in the pro game—stumbled at the finish line. Maybe Monica Seles' newfound dominance was to blame.

    Serving at 4-4 in the third, the German fell in a 0-40 hole with a double fault. From there, it was all Capriati. The teen closed out the match showing some steely guts of her own, racking up what would be her only win against Graf in 11 meetings. 

    Graf, ever gracious after defeat, related to Capriati's golden moment. "[My gold medal] helped me to believe in myself. I'm sure for Jennifer, it's going to help her a lot, even more."

    Well said, Steffi. Well said.

5: 2004 Athens Bronze Medal Match, Fernando Gonzalez (CHI) D. Taylor Dent (USA)

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    Gonzalez d. Dent 6-4 2-6 16-14

    Part of a formidable '04 American tennis squad that featured Andy Roddick, Venus Williams and Martina Navratilova, not many were paying much attention to Taylor Dent when the Athens Games kicked off.

    Dent, who was slated to play dangerous David Nalbandian in the first round until the Argentine pulled out with a shoulder injury last minute, ended up getting unheralded Canadian Frederic Niemeyer instead.

    That opened up the draw nicely for the affable Californian, who experienced a breakthrough season the year prior to the Olympics in which he won three titles. He took out a bunch of fellow unseeded-yet-dangerous floaters en route to losing in the semifinal round to Nicolas Massu.

    Gonzalez, on the other hand, had taken down tough guns Roddick and Grosjean before losing a gripping semi to Mardy Fish, and also paired with Massu, of course, to reach the doubles final—which was to be played later this fateful day.

    Little did Gonzalez know what he'd be getting into. After splitting the first two sets, the Chilean and his feisty American opponent waged a war of attrition from all parts of the court. Dent served and volleyed and chipped and charged, showing no fear in facing one of the most lethal shots the game's ever seen—Gonzalez' forehand.

    The 16th seed, meanwhile, put that forehand to good use, pounding it past Dent at the net routinely. He scrambled and scraped and even showed some deft skill around the net himself—check out the 5:10 moment in the clip provided. How'd Gonzalez pull it off? Tough to say. But he just seemed to want it that little bit more at the end than Dent. 

    One thing is certain: I'm sure after such an epic victory, bronze has never looked so much like gold. 

4: 2008 Beijing SF, Rafael Nadal (ESP) D. Novak Djokovic (SRB)

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    Nadal d. Djokovic 6-4 1-6 6-4

    When Rafa Nadal had to pull out of this year's Olympics, it was not just devastating for him and his country—but for the rabid fans who crave his fantastic matches, just like this one.

    With Federer already gone and the beatable Fernando Gonzalez waiting in the wings, Djokovic and Nadal knew that the gold medal hinged on this titanic semi. And they played like it, up until 12:21 in the morning, when a flubbed gimme overhead by Djokovic sent Nadal tumbling, reveling, backwards.

    Heading in, this had all the feel of a final. After being tested in his opener by Potito Starace, Nadal cruised through his next three rounds. Djokovic, meanwhile, faced tough battles in each match leading up to this mouth-watering semifinal clash.

    Even though the Spaniard entered the bout with a 9-4 head-to-head advantage, Djokovic was coming off a great week in Cincinnati, during which he rolled by Nadal in the semis.

    On a humid Beijing night, these two engaged in one of their typical matches—y'know, the ones that kind of redefine your image of how the pro game is played.

    Swapping huge baseline strokes, using every inch of the court, scrambling to balls that were seemingly completely out of reach... these two set the standard for their future 2011 and 2012 battles with this match. 

    While Nadal ended up capturing this match, Djokovic later claimed bronze with a straightforward victory over a downtrodden James Blake.

3: Athens SF, Justine Henin (BEL) D. Anastasia Myskina (RUS)

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    Henin d. Myskina 7-5 5-7 8-6

    Backhands flatter than Rafa Nadal's abs. Double faults and angry Russian screaming like a Dementieva in her prime. Chokes bigger than Oracene Price's latest weave. Everything, it seemed, that could be on display was on display in this unforgettable semifinal match.

    It was a battle between the year's Australian Open and French Open winners. In one of the strangest WTA seasons beheld, Henin collected the Melbourne major, got ousted in a shocking second round match from her beloved Roland Garros, withdrew from Wimbledon and then somehow miraculously made it to Athens (she'd end up sitting out the last part of the '04 season with an autoimmune disorder). 

    Myskina, meanwhile, had a brilliant run to the trophy in Paris and assembled a scintillating 11-2 summer record post-Wimbledon. She picked apart Francesca Schiavone in the quarters and nearly upstaged Henin in the WTA year-end championships the year before.

    Henin was the first to stumble in this thriller. Up 7-5 4-2 and cruising, she started to tighten up. Serves got shorter and forehands found the net. The Russian, in the midst of a career year, took advantage. She claimed the second 7-5 and, with solid, patient, yet aggressive baseline play, built a 5-1 lead in the decider.

    That's when the wheels fell off. Just needing to hold serve one more time, Myskina was broken in the seventh and ninth games of the hour-long final set. Henin, now, was the one closest to victory. Fighting off a 15-30 lead while serving at 7-6, she came up with some clutch deliveries to sneak away with an unthinkable victory. 

    The one biggest takeaway I have from this match is that it seemed to send Anastasia Myskina's promising career tumbling.

    Granted, the Russian dealt with threatening injuries and family grief during her '05 and '06 seasons (with a foot injury eventually ending her career for good), but this loss really took its mental toll.

    Always a fiery, mentally suspect player, the Russian never quite recovered from this shocker. Henin, meanwhile, went on to become the world's most dominant player—again—in the next few years to come.

2: 2008 Beijing SF, Fernando Gonzalez (CHI) D. James Blake (USA)

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    Gonzalez d. Blake 4-6 7-5 11-9

    No "top match" list of any kind is complete without some sort of controversy. 

    Which is why I present No. 2 on the list, Fernando Gonzalez (yep, him again) and his unbelievable semifinal win over James Blake at the '08 Beijing Games. 

    This was big-boy tennis played at its best—both guys were so much more concerned with playing for country than playing for themselves (or so it seemed).

    Much like Juan Martin Del Potro nowadays, Blake and Gonzalez were masters of the gigantic, flat forehand—and frequently ran around their one-handed backhands to smack it. They also possessed lethal serves when "on."

    As the highlights show, there was little between the two in the first couple of sets. But as the highlights don't show, unfortunately, there was a moment in this match steeped in controversy.

    It came deep in the epic third set, with Gonzalez serving down 8-9. The first point of the game, Blake pounded a forehand straight at the Chilean, who was at net. The ball flew long and was called out—but Blake saw it hit his opponents racket first, which would've given him the point.

    The umpire didn't see it, however, and the point stuck with Gonzalez—despite the fact that the American squarely appealed to his opponent to 'fess up and tell the truth.

    Blake didn't end up winning another game.

    Gonzalez capped off a three-hour win 11-9 in the third, booking a place in the gold medal championship against either Nadal or Djokovic.

    Fuming in his press conference, Blake had this to say: “Playing in the Olympics, in what’s supposed to be considered a gentleman’s sport, that’s a time to call it on yourself. Fernando looked me square in the eye and didn’t call it... That’s a disappointing way to exit the tournament when you not only lose the match, but you lose a little faith in your fellow competitor.”

    It's a difficult situation, and video replays at the time of the match confirmed Blake's allegations. But as Scoop Jackson wrote in a great recap, it's a controversy that shouldn't have happened. Blake had a 6-5 lead in the third set with three match points on Gonzalez' serve, but couldn't take advantage.

    Coming off a monumental victory over Roger Federer in the quarters, this was an especially bitter defeat for the American fan favorite. He lost out on bronze to Novak Djokovic.

1: 2008 Beijing F, Elena Dementieva (RUS) D. Dinara Safina (RUS)

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    Dementieva d. Safina 3-6 7-5 6-3

    Maybe it's not the most riveting match on this list. Or the cleanest. Or the most dramatic. But Elena Dementieva's memorable gold-medal victory in Beijing snags the No. 1 spot on my list because it exemplifies what the Olympics are truly about.

    For Dementieva, often referred to as the best female player never to win a Grand Slam, the Beijing Games were the highlight of a long and prodigious career.

    She broke through to the semis at the U.S. Open in 2000, reached two major finals in '04 and followed those up with numerous more clutch Slam semifinal appearances (including a few notable ones after winning the Games).

    Even though she never bagged the big one, representing Russia on a grand stage and taking gold felt just as good.

    In succession, she took down Caroline Wozniacki, Serena Williams, Vera Zvonareva and, in this classic bout, Dinara Safina to claim the gold. Not a bad lineup.

    Extracting revenge on her countrywoman in the final must have been extra sweet for Dementieva, considering Safina came back from 4-6, 2-5 and match points down to beat her in the French Open quarters just a few months prior.

    Despite riding an improved serve and a wave of confidence into the final, Dementieva was slow to start. She surrendered an early break as Safina loped around the back of the court, smacking winners with reckless abandon and hitting every corner of the service box. 

    The two kept up the big-babe tennis in the 66-minute second set, which had its share of unforced errors to balance out spectacular winners—but only because the two showed such athletic prowess, forcing each other to hit that one extra shot or go for just a little more than they were comfortable with.

    Safina aimed to go behind Dementieva with her most explosive weapon, the down-the-line backhand. Dementieva, meanwhile, was content to engage Safina in long, grueling cross-court rallies hoping to break down her compatriot's long strokes and wacky serve.

    It worked. In the third set, Safina held serve just once—succumbing to the nerves and exhaustion, owed in part to the fact that she'd been on court nearly double the time as her competitor due to doubles.

    Dementieva only got stronger—I only wish I could find a clip of Dementieva's 26th and final winner, a huge forehand that sent her to her knees in celebration. It's one the greatest, most visceral reactions the tennis world has ever seen.

    Following up on a silver medal earned in Sydney (and, ironically, taking advantage of 17 Safina double faults in the final), Dementieva lived out a dream.

    After winning, she summed it up perfectly: "I can't even compare a Grand Slam to the Olympic Games, it's just so much bigger. This is what I was waiting for. This is what I was working for. This is the biggest moment in my career, my life." 

Honorable Mentions

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    2000 Sydney SF: Venus Williams (USA) d. Monica Seles (USA) 6-1 4-6 6-3

    This all-American battle pitted new school versus old school for who would get a shot at the gold medal. Red-hot Williams was too much for Seles in the end, but the veteran did an excellent job making this competitive after getting blown out in the first set.

    2004 Athens 1R: Carlos Moya (ESP) d. Thomas Enqvist (SWE) 7-6(8) 6-7(7) 9-7

    One of the most vivid tennis memories I have from Athens comes, oddly enough, from this pretty obscure first-round match. Even though Moya was the third seed at the '04 Games, he still didn't seem a likely candidate for a marquee first-round television spot. But I'm glad they showed it.

    Enqvist, a former Top 5 player and Grand Slam finalist, was in the twilight of his career (and Moya was soon to follow). As a result, these two combined for some of the most visceral, physical, hard-fought tennis you could imagine.

    Moya ended up saving three match points in dramatic fashion—scraping out a 9-7 in the third victory. He later fell to eventual gold medalist Nicolas Massu in the quarters. 

    2004 Athens 3R: Mary Pierce (FRA) d. Venus Williams (USA) 6-4 6-4

    When Venus went back to defend her gold medal in Athens, she was in the midst of, arguably, the most disappointing season of her career. After breezing through her first two matches, the American was outclassed by a rejuvenated Pierce in every way in this hard-hitting encounter.

    Interestingly enough, this is when the first signs of Venus' autoimmune problems surfaced—recently, she recounted barely being able to breathe after points in this match against Pierce.

    2008 Beijing Doubles QF: Yan/Zheng (CHI) d. Kuznetsova/Safina 6-3 5-7 10-8

    This late-night epic transformed less into a tennis match and more into a rock concert in which the performers kept giving raucous encores. The longer the third set went, the louder the home crowd became in favor of their two-time Slam-winning doubles tandem.

    The match ended at 3:35 a.m.—talk about an overlooked stat. The Chinese saved a match point and ended up winning bronze.

    2008 Beijing Doubles SF: Aspelin/Johansson (SWE) d. Clement/Llodra (FRA) 7-6(6) 4-6 19-17

    Four hours and 44 minutes. For a three set doubles match. Incredible. The elder statesmen Swedes—Aspelin was 34, Johansson was 33—outlasted their flashy, talented French opponents, who were former Grand Slam champions.

    The most crushing aspect of this defeat may be that Clement and Llodra never even medaled for their effort. They were edged in three sets in the bronze medal match by the Bryan brothers. 

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