September 25, 1992: The day Jimmy Connors defeated Martina Navratilova in the “Battle of Champions”

On September 25, 1992, Jimmy Connors defeated Martina Navratilova in straight sets, 7-5, 6-2, in an event dubbed the "Battle of Champions." The exhibition marked the last high-profile contest between a male and female professional player. At the time of the match, Connors had recently turned 40, while Navratilova was approaching her 36th birthday.

The contest featured modified rules to balance the competition, allowing Connors only one serve and expanding Navratilova's court by half a doubles alley on each side. Both competitors entered as all-time greats, with Connors having spent 268 weeks as ATP world No. 1 and Navratilova holding 332 total weeks atop the rankings.