The Five Greatest Tennis Matches That Never Happened

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Famous Five: In the first of a new series, Martin Keady, our resident tennis historian, looks at a player, match or event from the world of tennis that is making the news and draws comparisons with similar players, matches or events from tennis history. This week, after “The Grapple in the Apple” between Nadal and Federer failed to materialise, he looks at some of the greatest tennis matches that never actually happened.

“The Grapple in the Apple” is such a memorable and poetic phrase that only Don King could have coined it–and he did, nearly a decade ago. The famously shock-haired boxing promoter, who named such legendary 1970s heavyweight boxing matches as “The Rumble in the Jungle” and “The Thrilla in Manila,” first came up with “The Grapple in the Apple” in 2008, when he was hired by the US Open to try and generate publicity for what was thought to be an inevitable New York clash between Roger Federer and Rafael Nadal. Nearly 10 years on, however, the two greatest male tennis players ever are still yet to play each other at the US Open and now may never do so. If that proves to be the case, then “The Grapple in the Apple” will take its place in the list of the greatest tennis matches that never actually happened.

Here are five others.


If Federer and Nadal are unarguably the two greatest male tennis players ever (statistically speaking, there is no argument), it is much less certain who are the two greatest female tennis players ever. Nevertheless, for all the rival claims of great players such as Martina Navratilova, Margaret Court, and Suzanne Lenglen, there is certainly a case to be made that the Williams sisters–Serena and Venus–are the two finest. If Serena returns from giving birth with her trademark intensity intact, she will surely overtake Court’s all-time Grand Slam singles record of 24 (she is currently just one behind at 23). Equally, Venus has reminded everyone this year, not least at the US Open this week, that if she had not been struck down with Sjogren’s syndrome (a debilitating ME-like illness) nearly a decade ago, she would surely have won more than her relatively meager seven Majors.

However, for all the brilliance that they have demonstrated against everyone else on the WTA tour, the Williams sisters have never truly demonstrated it against each other, and certainly not in the most important arena of all, a Grand Slam final. They have met in nine Slam finals in all, with Serena winning seven of them, including the most recent one, in Australia earlier this year. Of those nine finals, only two of them–the Australian Open this year and Wimbledon in 2003–have even gone to three sets and neither of them were authentic, undoubted classics.

Such is the strength of their sisterly bond that Serena and Venus have almost adopted a kind of “Team Williams” mentality, such that as long as one of them wins a tournament, it doesn’t really seem to matter which one. Ultimately, Serena has pulled far away from Venus, especially in the last 10 years, as Venus has struggled with her medical condition. Consequently, if Serena returns to somewhere near her best after returning to the tour, it is almost certain that we will never see the no-holds-barred, kicking-and-screaming, truly great Grand Slam final between the two of them that the tennis world has always hoped for.


Andy Murray had to win Wimbledon to finally receive the kind of adulation from the All-England crowds that Tim Henman received simply for reaching a succession of semi-finals. That is a testament to the historic importance of Henman, who, after decades of ignominious first or second-round Wimbledon exits by British players (particularly the men), proved that British men could actually compete at their home Major. Given that the hill at Wimbledon was famously renamed “Henman Hill” in his honour, despite his never actually reaching the men’s singles final, what on earth would his legacy have been if he had actually won Wimbledon? For a year or two at least, and especially in the UK’s tabloid headlines, it would surely have been renamed “Timbledon.”

Of course, the closest that Henman came to making the men’s singles final at Wimbledon was in 2001, when he lost in the semi-final to Goran Ivanisevic in a rain-affected match that had to be played out over a whole weekend. Ultimately, that match led to the addition of a roof to Centre Court. So, as well as the hill that is named after him, perhaps the Centre Court roof should also bear the Henman imprimatur. (It could be called “Tim’s Roof”, or just the “Troof” for short.)

What is conveniently overlooked in this alternative or fantasy history of Wimbledon, in which Henman wins the tournament 12 years before Andy Murray does, is the quality of the opponent he would have faced in the final if he had beaten Ivanisevic. The other semi-final that year was a repeat of the 2000 semi-final between Andre Agassi and Pat Rafter and was even better than the 2000 version (which itself was a classic), with Rafter finally winning 8-6 in the fifth. So, even if Henman had somehow defeated Goran to make the final, there is absolutely no guarantee that he would have overcome Rafter, another great serve-volleyer who had already won two US Open titles. Still, it’s fun to dream…


Astonishingly, the twin titans of women’s tennis between the two world wars, France’s Suzanne Lenglen and America’s Helen Wills Moody, played each other only once. That was largely because their careers did not really overlap, with Lenglen dominating women’s tennis for almost a decade after the end of WW1 and Wills Moody then replacing her at the top of the women’s game for most of the following decade. It was also partly because in the age before air travel, European and American players did not face each other nearly as often as they do now, with the individual Grand Slam events largely being won by home players. Typically, Lenglen triumphed in Paris and London, while Wills Moody dominated the US Open.

The one time that the two met was not even in the final of a Major, but in the final of a relatively unheralded (though still quite opulent) tournament at the Carlton Club in Cannes. It took place on 16 February 1926, when Wills Moody was only 20 and Lenglen a relatively venerable 26. According to the contemporary accounts, the match was something of a classic, with Lenglen winning in straight sets, 6–3, 8–6, but only after surviving a set point against her in the second set. Apparently, Wills Moody disputed a line call against her on that set point, but eighty years before the introduction of Hawkeye she could not have the decision over-ruled.

If it is astounding that Lenglen and Wills Moody only met once, it is perhaps even more amazing that, after such a fine match between them, there was never a rematch, either at the Majors or anywhere else. Like Wills Moody’s set point, the reasons for that are disputed, with one theory being that Lenglen’s father advised his daughter never to play Wills Moody again, fearing that the American would undoubtedly win a rematch. Whatever the reason, these two greats of the women’s game never played each other again, as Lenglen turned professional at the end of 1926 and Wills Moody was effectively left to rule the amateur women’s game for the next decade or so.


In a BBC radio interview with Paul Annacone during this year’s US Open, it was fascinating to hear the great coach, who has worked alongside both Pete Sampras and Roger Federer, making comparisons between the two men. In particular, he said that although both were born winners, Federer’s more easy-going personality and sheer love of the tour set him apart from Sampras, who was much more private and intense than the Swiss and consequently quit tennis much earlier.

Of course Sampras did so having failed to complete the career Grand Slam of winning all four Majors, as he never won the French Open. He was not alone among great American players in failing to win in Paris, with John McEnroe being the other obvious example, but at least McEnroe made the final at Roland Garros, playing probably the finest two sets of serve-volley tennis ever seen on clay before succumbing in five sets to Ivan Lendl in 1984.

The closest that Sampras ever came to winning the French title was in 1996, when he reached his only semi-final in Paris. Having defeated both Sergi Bruguera and Jim Courier, who had both won the French Open twice before in the previous five years, Sampras was the strong favourite against Russia’s Yevgeny Kafelnikov. What followed was perhaps even more astonishing than McEnroe’s late collapse against Lendl 12 years previously, as Kafelnikov not only won in straight sets but actually bageled the great Sampras 6-0 in the second set.

Sampras never came close to winning in Paris again, instead perfecting his serve-volley game at the other, faster Majors – Australia, Wimbledon and the US Open–which he won a total of seven more times. Nevertheless, the absence of a French Open title from his otherwise stellar CV remains the major argument against him when it comes to arguments about who is the greatest male tennis player ever.


The No.1 on this fantasy list of great tennis matches that never actually happened has to be the greatest Wimbledon women’s final that never actually happened–the 1993 final between Steffi Graf and Monica Seles, which would have been a contest not only for the Wimbledon title itself but for the undisputed dominance of the women’s game, perhaps for the next decade.

That Monica Seles did not reach the Wimbledon final that year, or indeed even play at The Championships, was of course due to the terrible injuries and shock that she suffered after being stabbed by a fanatical Steffi fan at a tournament in Hamburg on 30 April, barely two months before the start of Wimbledon. As a result, Seles had to withdraw from Wimbledon and it was ultimately more than two years before she returned to the WTA tour at all. And when she did return, she was–entirely understandably–never quite the same great player again, winning only one more Grand Slam tournament (the 1996 Australian Open) to go alongside the eight Majors that she won before she was attacked.

Of course, just as Sampras never won the French Open, Seles never won Wimbledon, but unlike Sampras Seles at least made the final of the Grand Slam she never won, facing Graf in 1992, although she lost rather meekly in straight sets, 6-2, 6-1. However, if she had been able to play at Wimbledon the following year, there is every chance that she would have made the final again and almost certainly made a better fist of it. She might even have beaten Graf, who was certainly not at her best in 1993. Indeed, Graf nearly lost to Jana Novotna before Novotna’s great “choke” with the winning line in sight, and the ruthless Seles would surely never have let Graf off the hook.

Like all these fantasy or imaginary matches, and like the much-vaunted and much-anticipated “Grapple in the Apple,” the 1993 Wimbledon Final between Graf and Seles never actually took place. If it had, and if Seles had won, then women’s tennis for the rest of the 1990s and even into the early 2000s might have been very different, with Seles completely dominating the women’s game and winning the 20-plus Majors that Graf ended up claiming. It is a testament to the greatness of Seles that she won even one Major after her awful attack, but, like all the players on this list, she might have won so much more.