Serena vs. BJK, Evert vs. Barty, Graf vs. Sharapova: Across 50 years, imagine these match-ups between WTA greats

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The WTA’s 50 years have seen a swath of great champions and playing styles. It has led to iconic rivalries and memorable matches from yesteryear we still rabidly discuss today. But what about matches that can only take place in the imagination, pitting various titans across that half-century against one another? How would the rallies shake out? In the interest of the best possible tennis, which playing surface is mutually favorable?

For expert commentary, we asked five members of the “Original Nine”—the Hall of Famers who in 1970 started the professional women’s tour—for their thoughts.

Serena Williams vs. Billie Jean King

• Singles majors: Williams 23, King 12

Two of the best pressure players ever dare one another to come up with the goods. Williams generated tremendous power, most notably with the greatest serve in the history of women’s tennis and forceful groundstrokes. She also had excellent court coverage skills. “Serena was as fast as anybody I’d ever seen,” according to Julie Heldman. King also moved exceptionally well, employed a wide range of speeds and spins, and volleyed as proficiently as anyone who’s ever played the game. “Serena would overpower Billie Jean,” said Kristy Pigeon, “But Billie Jean would move her around the court past her comfort level.” Another psychological factor also figures into the mix. “These two are both such great competitors and very emotional,” said Valerie Ziegenfuss. “So it gets down to who can best control their emotions.”

Since these two collectively won 13 Wimbledon singles titles (seven for Williams, six for King), let’s put this match on Centre Court and see who indeed can meet with triumph and disaster and treat those two imposters just the same.

Chrissie Evert vs. Ashleigh Barty

• Singles majors: Evert 18, Barty 3

Over the course of a short time at the top of the game, Barty thrilled tennis aficionados with her wide range of shots and graceful movement. “Barty would frustrate Evert with greater shot variety,” said Pigeon. There’s a natural stylistic comparison between Barty’s game and the style of her tennis hero, fellow Australian Evonne Goolagong—a player who also happened to be Evert’s first great peer-level rival. Evert’s strength was her sustained depth and accuracy off the ground.

The way Heldman views this matchup? “Evert had played against many attacking players like Evonne, Billie Jean, Martina and Virginia Wade, so she was aware of what she’d need to do ... her shots would be so accurate and reliable that there were no holes.” One other factor is that both were exceptionally poised and unflappable.

Said Richey, “Barty had every bit as good a temperament as Evert.” Such are the dynamics of this matchup that it’s easy to imagine them playing one another on any surface.

Martina Navratilova vs. Naomi Osaka

• Singles majors: Navratilova 18, Osaka 4

As with King versus Williams, this is a match-up between a powerful baseliner with a big serve and an all-courter with superb volleys. “Osaka when she was playing well hit the ball early and hard,” said Heldman. Said Casals, “If Naomi is on, she is really on.” One fascinating aspect: Osaka’s aggressive service returns versus a frequent net-rusher—a style she’s never encountered. Then again, as Ziegenfuss noted, “there’s not enough data yet on Osaka.”

Meanwhile, at Navratilova’s end, plenty is known about her athletic strengths: coordination, movement, and the ability to relentlessly apply pressure to her opponents. It took a little while, but once Navratilova had all the pieces of her game together in the early 1980s, she was nearly unbeatable for many years. “Martina would have been able to take time away from Naomi,” said Heldman. “Her swinging lefty serve would have gotten Osaka in trouble.”

Given these many factors, let’s put this one on a hard court.

Stefanie Graf vs. Maria Sharapova

• Singles majors: Graf 22, Sharapova 5

Here’s a match between two players who always conducted themselves with exceptional urgency. In other words, there’s no need for a serve clock. Both were willful and strong off the ground, Graf usually with her forehand, Sharapova off the backhand side. “It’s kind of a toss-up,” said Richey. “Sharapova can clean your clock,” said Casals.

One key tipping point area is the matter of court coverage. According to Ziegenfuss, “Sharapova was a great competitor, but not as good a mover.” The result of that contrast is that while Sharapova often felt the need to take charge of the rallies early, Graf’s exceptional footspeed allowed her to stay more patient. “Graf didn’t make as many mistakes,” said Casals.

With each of these players looking to dictate the tempo rapidly both during and in-between points, imagine them competing versus one another on tennis’ preeminent first-strike surface, grass.

Margaret Court vs. Iga Swiatek

• Singles majors: Court 24, Swiatek 4

When in peak form, Margaret Court overwhelmed her opponents with reach, agility, movement and power. “I could play well against her,” said Ziegenfuss, “and get one game.” Said Casals, “She was like a train. Once got going, she was moving.” This is quite similar to how Swiatek has earned many of her victories, smothering opponents with athleticism, footwork, and one sharp placement after another.

One of Court’s cornerstone shots was a laser-like backhand slice—precisely what’s needed to attack Swiatek’s Western grip off the forehand side. On other hand, Court’s serve could be up and down, perhaps the result of her playing right-handed despite being a natural lefty. “It went in streaks,” said Ziegenfuss.

That could prove quite difficult versus a returner as aggressive as Swiatek. So far in her career, Swiatek has won three of her four majors at Roland Garros. Court won the singles title there five times. Assign these two to Court Philippe-Chatrier.