September 25, 1992: Jimmy Connors Defeats Martina Navratilova in "Battle of Champions"

On September 25, 1992, Jimmy Connors faced Martina Navratilova in a highly publicized exhibition match dubbed the "Battle of Champions" at Caesars Palace in Las Vegas. Connors, an eight-time Grand Slam champion and holder of 109 singles titles, was known for his flat, baseline game, heavily influencing future generations.

Connors turned professional in 1972 and reached world No. 1 in 1974, winning three Grand Slams that year despite being barred from the French Open. He held the top ATP ranking for a then-record 160 consecutive weeks and a total of 268 weeks. After a dip in performance, Connors reclaimed the No. 1 spot and won three more Grand Slams in 1982 and 1983. He remained a top-10 player until age 37, concluding his career with 109 tour titles, including eight Grand Slams.

Martina Navratilova, born in 1956, was acclaimed as arguably the greatest player ever in singles, doubles, and mixed doubles. Since the Open Era began in 1968, she held records for most singles (167), doubles (177), and total matches won (2189). Navratilova secured 18 Grand Slam singles titles, including a record nine Wimbledon crowns, and achieved a then-record 332 weeks at world No. 1. By 1992, she also had 31 Grand Slam doubles titles and six in mixed doubles, narrowly missing the career "Boxed Set Grand Slam" (winning all four majors in singles, doubles, and mixed doubles).

The "Battle of Champions" took place at the Las Vegas hotel and casino Caesars Palace. The event, unlike the politically charged "Battle of the Sexes," was primarily an entertainment spectacle, with each player earning $500,000, with prize money doubling for the winner. The match was broadcast on pay-per-view.

To level the playing field, modified rules were implemented: Connors was allowed only one serve, and Navratilova could hit into the first half of the doubles alley. Connors approached the match with his characteristic intensity, stating, "You consider it fun. I consider it my job playing against Martina. And it’s not as easy as you think."

In front of over 13,000 spectators, the match saw Connors serve at around 65 mph. Despite an initial deficit, Connors broke Navratilova's serve and won the first set 7-5 after 52 minutes, with Navratilova making 26 unforced errors. Connors secured the second set more easily, 6-2, as Navratilova struggled to adapt to the adjusted court space. After the match, Connors expressed willingness for future similar events but without the extended court, citing the "too much running" for a 40-year-old. Navratilova admitted to unprecedented nervousness, calling the experience unlike anything she had faced before.

This exhibition was the last of its kind. While other cross-gender challenges occurred later, none matched the scale or public attention of this event. Years later, in 2013, Connors revealed he had bet $1 million on himself to win in straight sets without losing more than eight games, potentially explaining his slow start.