Martina Navratilova and Serena Williams only crossed paths for a brief period in their respective careers.
Williams won the US Open in 1999, where she beat Martina Hingis to win her first major singles title at 17-years-old.
At this point, Navratilova had announced her retirement, before making a comeback to the WTA Tour in 2000.
Navratilova officially retired in 2006 at 49-years-old, but was never able to play a singles match against Williams.
Photo by Dan Istitene/Getty ImagesWhat Martina Navratilova predicted would have happened if she faced Serena Williams in 2003
Three years before her final farewell in 2003, Navratilova spoke to the Guardian about Serena Williams, who was a six-time Grand Slam champion at the time.
In this interview, Navratilova was asked about how a hypothetical match between Williams and herself at her 1980’s peak would have gone.
Jul 1987: Martina Navratilova of the USA holds up the winner plate after winning the Wimbledon Championships played at Wimbledon, London, England. Mandatory Credit: Allsport UK /Allsport
Navratilova won 15 of her 18 major singles titles in the 1980’s, and backed herself to at least win some matches against Williams.
However, Navratilova admitted that Williams had the potential to have a better career than her.
“I would certainly win some matches . . . but so would she,” said Navratilova. “It’s real tough to say who would win more.
“I think if she ever reaches her potential she could be better than I was – but tennis is about so much more than just pure ability. Serena is still learning about the game. A lot depends on how much she wants to stretch herself.
“Ironically, she and Venus featured in my list of goals at the start of the year. I aimed to win another Grand Slam and to make it to the Fed Cup. The third aim was to beat the Williams sisters – but I never got the chance to play them. Maybe next year?”
Williams retired 19 years later in 2022, finishing her career with 23 Grand Slam singles titles, the most of any woman in the Open Era.
What happened when Martina Navratilova played the Williams’ sisters in doubles?
After she officially retired, Navratilova admitted Serena was her dream opponent, despite never being able to play her in singles.
Although she was never able to fulfill her dream match in singles, Navratilova did twice go head-to-head with Serena and Venus Williams in doubles.
The first of those meetings came in the quarter-finals of Wimbledon in 2000, where Navratilova partnered South African Mariaan de Swardt.
Despite winning the first set, Navratilova and De Swardt were unable to beat the exciting young American sibling duo of Serena and Venus, who won 4-6 6-2 6-1.
Photo credit should read MARTYN HAYHOW/AFP via Getty Images
After beating Navratilova and De Swardt, the Williams sisters would go onto win their first Wimbledon title together that year.
They would go head-to-head at another Grand Slam tournament three years later, this time Navratilova would partner Svetlana Kuznetsova at the Australian Open.
This was a much more one-sided affair, as the Williams sisters dropped just five games en route to winning another Grand Slam.