Dream Matchups Between Current and Past Tennis Stars
Arguing a player’s legacy against another’s is one of the greatest discussion points in any sport.
As such, I have selected five dream matches between current and past tennis stars that fans would surely loved to have seen.
When comparing players from different generations, though, there are a number of things to consider: the advancements in technology and sports science, the progression of rackets and the slowing down of surfaces.
While I have considered these contrasting effects between players in different eras, it would spoil the fun to focus too heavily on them.
I will also be discussing and comparing the two players at their peak rather than at any comparatively weak points in their career.
Thankfully, only one of the five pairs actually played against each other at the opposite ends of their careers, leaving much of it to our wonderful imaginations!
Andy Murray-Pete Sampras
1 of 5
Down the years, you will surely have heard the argument that Andy Murray is a victim of timing.
Pitted alongside three indisputable all-time greats, the Scot has certainly had to do things the hard way: All eight of his Grand Slam finals have been against Roger Federer or Novak Djokovic, while Rafael Nadal has beaten him in six Slam semi-finals.
Had Murray played in a comparatively weaker era—such as the 1990s—he would surely have romped home to numerous Slams.
Or so the argument goes.
But would Murray have been as good as he has become without intense competition and multiple setbacks to drive him forward?
And would he have been as effective on quicker surfaces?
The best indicator would be if we could pit Murray against Pete Sampras, undoubtedly the dominant player of the '90s with 12 Slams (as well as a couple more in the early 2000s).
Given the contrasting styles of the duo, the surface would be particularly crucial in terms of the winner of the contest.
Grass, in particular, was faster in Sampras’ era, helping both his first and second serve stay problematically lower.
But how would Sampras’ clockwork serve-and-volley have fared against a quick-fire returner like Murray?
Again, the surface would make a huge difference; on today’s, Murray would be able to manipulate points in his favour easier than on one where a higher percentage of serves would prove unreturnable.
But given Sampras had a 20-14 career record against Andre Agassi, who is regarded as perhaps the finest returner ever, I’d underestimate the American at your peril.
In his dominant prime, he may have just had a bit too much for Murray.
Novak Djokovic-Andre Agassi
2 of 5
What a slugfest this would have been!
Novak Djokovic’s triumph at the Australian Open last month took him level with Andre Agassi on eight Slams.
It also took him one past Agassi’s total of four Australian Opens.
Unlike Agassi, though, Djokovic is still searching for that illustrious career Slam, with Rafael Nadal perennially standing in his way at the French Open.
There are similarities between Djokovic and Agassi that would make for a fascinating contest.
Neither will be remembered as excellent servers (though, like Agassi as he grew older, Djokovic’s is continuously improving), as both preferred to prolong points in order to tire their opponents and dictate play.
As such, had they had the chance to have played each other at their peaks, they may well have endured a longer Slam final than Djokovic and Nadal's record six-hour Australian Open final in 2012.
Both will also be remembered as two of the finest returners in the history of the sport.
When asked in 2013 how he would have beaten Djokovic had they have had the chance to play against each other, Agassi replied, as per The Guardian, "I would have probably gotten in a fight with him in the locker room before the match. I might have had a chance there."
While typically jovial, his next comment was more revealing, as he said, "I would have had to be a different player, would've had to have a different body.”
The American was probably onto something there. The game has already advanced so much since Agassi retired in 2006 that it is difficult to imagine him even at his peak coming out on top against the Serb.
As Agassi told The Australian, when comparing and contrasting Djokovic to other great defenders he played against, such as Michael Chang and Lleyton Hewitt, “When [Djokovic is] on defence he can actually win the point with one shot.
"That's an evolution of the game."
Serena Williams-Steffi Graf
3 of 5
Serena Williams’ triumph at the Australian Open last month took her to 19 Grand Slam titles, placing her ahead of Chris Evert and Martina Navratilova and second only to Steffi Graf’s incredible tally of 22.
Williams admitted earlier this month that catching Graf inspires her, according to Jonathan Liew of The Telegraph. “It is definitely something that motivates me," Williams said. "A part of me feels like I have a chance to really create history.”
The pair, unlike any other in this list, actually faced each other twice in 1999—fittingly, the year of Graf’s last Slam title (and retirement) and Williams’ first—with Williams notably defeating Graf in the Indian Wells Masters final to win only her second WTA title at the time.
Both players are recognised as having two of the greatest forehands in the history of the women’s game, with Graf’s inside-out shot particularly deadly.
That said, Graf’s tendency to position herself on the backhand side—relying on her court speed to reach her forehand side—could have been routinely exposed by Williams’ phenomenal power.
Indeed, the American would surely look to keep points as short as possible against the German, whose excellent sliced, skidded backhand and unparalleled athleticism would undoubtedly frustrate Williams if allowed.
Ultimately, it is difficult to disagree with Brad Gilbert’s verdict for ESPN in 2013. “Even though Steffi dominated on the hard courts," Gilbert said, "her chances of beating Serena with any kind of regularity would be on clay.
“On any kind of faster court, it's still a great matchup of offense and movement, but with all that power from Serena, especially on the serve, she's a favourite.”
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Rafael Nadal-Rod Laver
4 of 5
Only six men have won 10 or more Grand Slams in the Open era.
Only two of them were left-handers: Rod Laver and Rafael Nadal.
While their playing styles were different in many ways—to be expected when playing in entirely different eras—Paul Newman, for The Independent, wrote of a certain similarity, saying, "Laver used heavy topspin on both flanks and, like [Nadal], benefited from a huge left arm.
“Laver’s left wrist measured 7in around (an inch more than his right) and his left forearm, which at 12in is an inch and a half longer than his right, is the same size as [former heavyweight boxer] Rocky Marciano’s.”
Clearly, then, this dream matchup would not be one lacking in power and robustness whatsoever.
Moreover, Laver remains the only male to achieve the Grand Slam (all four Slams in one season) in the Open era, while Nadal joins him as two of seven elite players to have achieved a career Slam.
As such, it would be an intriguing matchup on any surface.
Laver himself told Newman, meanwhile, that he believed left-handers have an advantage in tennis.
“Lefties generally seem to have more spin ability than a right-hander. When they serve, they have a little bit more activity on the ball," he said.
“And when you’re down 30-40 on serve, where does your best serve go? It can go way out wide, most times to a right-hander’s weaker side.”
With this perceived advantage cancelled out in this dream matchup, it would be fascinating to see who would prevail out of the two finest lefties in history.
Ultimately, given they peaked four decades apart, it is almost impossible to determine who would have come out on top.
Roger Federer-Bjorn Borg
5 of 5
The parallels were drawn throughout Roger Federer’s rise to becoming recognised as the greatest player of all time.
Borg’s record of 11 Grand Slam titles was smashed, while the Swede’s five consecutive Wimbledon titles were also matched in 2007, with Federer overcoming Rafael Nadal.
That occasion even brought Borg back to Wimbledon for only the second time since retiring at the early age of 26 in 1981.
Both players are noted for their unique grace and composure on the court—although Borg’s rock star, ‘Ice Man’ image gave him more (largely unwanted) attention off it.
Borg himself commented on the similarities in the duo’s personality in 2007, as per The Telegraph, saying, "I see a lot of myself in Roger, as we're very similar on the court.
"He doesn't show his emotions either, he doesn't let it all out. He keeps his cool.”
The immense respect is certainly mutual.
It would be fascinating, then, to see arguably the two most naturally gifted players in tennis history—with ice running through their veins—face off against each other.
On clay, you’d probably back Borg’s innovative topspin, athleticism and ability to work his way into points.
On the other hand, Federer, by Borg’s own admission in that interview in 2007, was the “complete player on a grass court.”
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