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By this day in 1988, dating back to 1973, Martina Navratilova and Chris Evert had played one another 79 times. Amazingly, 59 of those matches had been in finals.

Now, the two were set to meet once again in the finals, this time in the Virginia Slims of Chicago tournament. A month earlier, Navratilova had turned 32. A month hence, Evert would celebrate her 34th birthday.

But 1988 was also the first year since ’73 that neither Evert nor Navratilova had won a Grand Slam singles title. For ‘88 marked the incredible ascent of Stefanie Graf, the 19-year-old German winning all four major singles titles, as well as the Olympic tennis event, to capture what was dubbed, “The Golden Slam.”

With Graf absent from the Chicago field, Navratilova and Evert were the top two seeds. Each smoothly made her way to the finals, Navratilova without the loss of a set, Evert only dropping the second set of her semifinal against fourth-seeded Manuela Maleeva.

Evert had won the title in Chicago once, back in 1977 beating Margaret Court in the finals. Navratilova had fared even better in the Windy City, winning there eight times, including six straight from ’78-’83 and two more in ’86 and ’87. The fast indoor carpet was a natural fit for her attacking playing style.

This would be the third time the two greats played one another in Chicago. Navratilova had won both prior matches, in ’75 beating Evert in the semis, in ’80 winning the final.

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Navratilova and Evert played their 14th major final at Roland Garros in 1986, where Evert triumphed in three sets.

Serving superbly, Navratilova lost just four points on her serve in the first set, handily winning it, 6-2. She took the second set by the same score. Said Evert in a Los Angeles Times story about the match, “Her serve was a real weapon on a court this fast. I don’t have a weapon like that. I’d have to do everything perfect to beat her on this kind of surface.”

“I enjoyed winning, but I know Chris was not playing as well as she could,” said Navratilova. “I don’t know how much I had to do with it or how much she had to do with it. It really wasn’t a thrilling match.”

Navratilova would finish ’88 ranked second, one spot ahead of Evert. Yet through the first eight months of ’89, the two did not play one another once. In late August, Evert announced that the US Open would be her last tournament. The draw revealed a potential Evert-Navratilova semifinal matchup. But Evert lost in the quarterfinals to Zina Garrison.

So it was that Chicago proved the last meeting of the incredible Evert-Navratilova rivalry. They’d first met as teenagers, the 18-year-old Evert beating the 16-year-old Navratilova, 7-6, 6-3.

That initial match had taken place in Akron, Ohio. How remarkable that for all matches the two had gone on to play, going toe-to-toe frequently at all four majors, in cities and arenas all over the world, that their final match would be less than 400 miles from where it had all started.