The greatest matches that never happened

Published by Matt Trollope

Naomi Osaka (L) and Serena Williams were just one point away from clashing in a blockbuster Australian Open 2019 semifinal (Getty Images)
Several projected showdowns – whether due to the rivalry, the context, or the players’ form – could have been the greatest matches in tennis. But due to one player losing, they never happened.

When the draws come out for Grand Slam tournaments, projecting blockbuster match-ups is a common exercise.

And when those two players continue to win and get closer to a highly-anticipated showdown, excitement grows.

Sometimes, we get so close to a match-up everyone wants to see, only for something to conspire against it. Here’s a look at some Grand Slam matches that promised so much had they eventuated, but ultimately never did.  

Naomi Osaka v Serena Williams – Australian Open 2019 semifinals

This might border on hyperbolic, but make no mistake – had Serena Williams converted one of her four match points in this year’s Australian Open quarterfinals against Karolina Pliskova, it would have set the stage for one of the more highly-anticipated women’s tennis matches in history. And in a WTA era where truly great rivalries have failed to materialise, this would have been a step in the right direction.

Everyone knows what unfolded when she and Naomi Osaka last met; the Japanese youngster went on to upstage her idol in the US Open final to become a Grand Slam champion. The context surrounding the near-rematch, and the questions it would have raised, were tantalising.

How would Williams respond against an opponent who was no longer the challenger, but now a considerably higher-ranked player and a reigning major champion? Would Osaka become the first woman in history to build a winning 3-0 head-to-head record over Williams? Who would overpower the other? Who would the crowd side with? What would the handshake be like? And how would the media coverage unfold in the build-up? Both women had deftly side-stepped any discussion of their US Open final four months earlier, yet that discussion would have become unavoidable had they met in the semifinals.

But they didn’t. Pliskova rallied from 5-1 down in the third set to upstage Williams, and took her place across the net from Osaka in the semifinals. It ended up being a fabulous match; in fact, one of the best of the tournament. But the sporting world was denied an unmissable spectacle.

Roger Federer v Rafael Nadal – US Open, almost every year

Roger Federer and Rafael Nadal have played 38 times. Twelve of those meetings have come at Grand Slam tournaments, including in the finals of the Australian Open, Roland Garros and Wimbledon. Yet they have never met at the US Open.

This is one of the more mystifying tennis statistics, given that on six occasions, the celebrated duo have come within one win of facing off at Flushing Meadows, only for one of them to lose. Here’s a look at how that has unfolded:

2008 Federer won his semifinal, yet Nadal lost his to Andy Murray
2009 Federer won his semifinal, yet Nadal lost his to Juan Martin del Potro
2010 Nadal won his semifinal, yet Federer lost his to Novak Djokovic – despite holding two match points
2011 Nadal won his semifinal, yet Federer lost his to Djokovic – again after holding two match points
2013 Nadal won his fourth-round match, yet Federer lost his to Tommy Robredo, who then fell 60 62 62 to Nadal
2017 Nadal won his quarterfinal, yet Federer lost his to Juan Martin del Potro.

The more times these near-misses occur, the more the appetite builds to see Federer and Nadal clash on the biggest tennis stage in America. Yet it seems the sports gods are determined not to let that happen.

Rafael Nadal v Novak Djokovic – Roland Garros 2011 final

One will always wonder how Rafael Nadal would have fared in the 2011 Roland Garros final had he come up against the white-hot Novak Djokovic rather than Roger Federer, a player far less threatening to the Spaniard on clay.

Djokovic went unbeaten in the first five months of that season in one of the most dominant stretches recorded by a player in the Open era. During that period he beat Nadal four times – in the finals at Indian Wells, Miami, Madrid and Rome – and would later beat him again in the Wimbledon and US Open finals. He was in Nadal’s head.

Djokovic’s winning streak extended to 41 matches when he beat Richard Gasquet in the last 16 in Paris, but when quarterfinal opponent Fabio Fognini withdrew, the Serb was forced to wait four days – extremely unusual for a Grand Slam event – before taking to the court again. Federer, still in the groove of a day-on, day-off schedule, played brilliantly to upset Djokovic when they met in an electric four-set semifinal, emphatically waving his index finger as the crowd roared following match point.

Yet the final, predictably, ended with a Nadal victory; the Spaniard won 6-1 in the fourth. Nadal is a perfect 11-0 in Roland Garros finals (four of those victories coming over Federer) and has never been pushed to five sets in any of those finals. It may have been a different – and more compelling – story had he faced Djokovic that year instead.

Serena Williams v Maria Sharapova – Australian Open 2008 semifinals

Few times has Maria Sharapova looked more devastating in her career than during the Australian Open 2008 fortnight. The Russian mowed down all opposition, not dropping a set to win her third Grand Slam title. The ferocity of her shotmaking, the intensity of her focus and her general swagger and confidence all peaked during this tournament.

She and Serena Williams were on a semifinal collision course, yet when Sharapova dissected world No.1 Justine Henin 6-4 6-0 to reach the last four, her opponent was instead Jelena Jankovic, who had upset Williams earlier that day. At that point in their head-to-head series – which would ultimately become completely one-sided – Williams led Sharapova by a much slimmer margin of 4-2, and had yet to inflict many of the mental wounds Sharapova now nurses when facing her nemesis.

Who knows what might have unfolded had this version of Sharapova come face to face with Serena at Rod Laver Arena? Given the one-sided nature of most of their meetings, this one seemed to have all the ingredients necessary for a truly memorable encounter.

Lleyton Hewitt v Roger Federer – Australian Open 2005 final

Hewitt’s run at the centenary edition of the Australian Open had whipped his home country into a frenzy; viewership figures soared as he cut down a succession of quality opponents – Rafael Nadal and David Nalbandian in five sets, Andy Roddick in four – to reach his first final at Melbourne Park.

The prospect of a final meeting with world No.1 and defending champion Roger Federer would have been one of the biggest sporting events in the nation’s history. But instead, he played Marat Safin – certainly a celebrated player, but not one with Federer’s profile – in the decider. A night earlier, Safin had saved a match point to beat the Swiss star 9-7 in the fifth set. It was just the second time Safin had upstaged Federer in eight meetings, and it would be the last – Federer won their next four encounters, dropping just one set in the process, to dominate the overall head-to-head series 10-2.

Safin went on to break Australian hearts in the final, recovering from a set down to beat Hewitt in four sets for his second and final major title.

Pete Sampras v Andre Agassi – Wimbledon 2000 final

Sampras v Agassi was the Federer v Nadal of its day. This rivalry had every ingredient necessary – contrasting styles, distinct personalities and no love lost between them – to captivate the public’s interest, and it did, all through the 1990s and into the early 2000s. Sampras ended up 20-14 ahead after their 34 meetings, although they split their last eight matches.

They came within one set of facing off in a blockbuster 2000 Wimbledon final, which would have seen Sampras gunning for a then-record 13th Grand Slam singles title, with Agassi desperate to turn the tables after losing their 1999 Wimbledon decider. He had since beaten Sampras in their most recent Grand Slam meeting, a five-set thriller in the Australian Open semifinals. On top of that, a Sampras v Agassi clash would have pitted the tournament’s top two seeds against one another.

Yet it never eventuated. Australia’s Pat Rafter saw to that, beating Agassi 7-5 4-6 7-5 4-6 6-3 in the semifinals, a year on from losing to Agassi in straight sets at the All England Club, also in the semifinals. Rafter provided some resistance against Sampras in the subsequent final, but went down in four sets.

Martina Navratilova v Chris Evert – Australian Open 1984 final

Had Navratilova defeated teenager Helena Sukova in the Australian Open semifinals, she would have had a shot at the calendar-year Grand Slam against her greatest ever rival. You could barely write a better script. And given their two major finals on either side of that – the 1984 US Open and 1985 French Open – were both barnstorming three-set affairs, you could practically guarantee a Navratilova-Evert clash would be a magnificent spectacle.

Except Navratilova fell 7-5 in the third set to Czech Sukova, after winning the first set 6-1. It was an astounding upset, given the form Navratilova carried into the semifinals. She was unbeaten in 74 matches and had won an extraordinary six consecutive Grand Slam titles spanning 1983 and 1984. And in another example of Navratilova’s dominance, she had never dropped more than three games in a set against Sukova in three previous meetings.

All that changed in that December of 1984, and Sukova advanced to her first ever major singles final, preventing Navratilova from becoming the first player to win a record seventh straight major title. Sukova then fell to Evert in the final, although it did extend to three sets.

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