Battle of Sexes: List of winners in male vs female tennis match since 1973

The concept of inter-gender matches began with Bobby Riggs taking on Margaret Court in 1973, even before the first-ever Battle of the Sexes match

The tennis action for the year 2025 is set to close out today with Aryna Sabalenka taking on Nick Kyrgios in only the second-ever Battle of the Sexes match in tennis, at Dubai’s Coca-Cola Arena, since the first match between Billie Jean King and Bobby Riggs back in 1973.

 

Both players have a strong fan base, making Sunday’s game a much-anticipated event. However, while this will only be the second tennis match titled Battle of the Sexes, it’s not just the second-ever inter-gender match in tennis. The concept of inter-gender matches began with Bobby Riggs taking on Margaret Court even before Billie Jean King and has been used on many other occasions.

 

 

Now, before Sabalenka and Kyrgios square off in an epic battle in Dubai, let’s take a look at all the winners and participants of every male vs female tennis match over the years. 

Full list of winners in male vs female tennis matches:

Match	Date	Format	Result	Venue/Context
Margaret Court vs Bobby Riggs	13 May 1973	Best of 3 sets	Riggs won 6–2, 6–1	Houston, played on Mother’s Day
Billie Jean King vs Bobby Riggs	20 Sep 1973	Best of 5 sets	King won 6–4, 6–3, 6–3	Houston Astrodome, 30,000+ crowd
Martina Navratilova vs Jimmy Connors	25 Sep 1992	Best of 3 sets	Connors won 7–5, 6–2	Las Vegas, Caesars Palace exhibition
Karsten Braasch vs Serena Williams	1998	1 set	Braasch won 6–1	1998 Australian Open side challenge
Karsten Braasch vs Venus Williams	1998	1 set	Braasch won 6–2	1998 Australian Open side challenge
Serena Williams vs Andy Murray	2019	—	—	Proposed exhibition, did not materialize

 

Margaret Court vs Bobby Riggs (1973)

 

Before his headline-grabbing clash with King, Bobby Riggs first challenged then world No. 1 Margaret Court on May 13, 1973. The match, played on Mother’s Day, later earned the nickname “Mother’s Day Massacre” due to Riggs’ one-sided 6–2, 6–1 victory. Using heavy spin, slices and unconventional shot-making, Riggs capitalised on Court’s nerves and controlled the tempo throughout. The defeat played a key role in convincing Billie Jean King to take on Riggs months later, setting the stage for the match that would reshape tennis history.

 

Martina Navratilova vs Jimmy Connors (1992)

 

Martina Navratilova and Jimmy Connors met in a widely publicised exhibition on September 25, 1992, in Las Vegas, promoted as “The Battle of Champions”. The contest included experimental rules to level the conditions, with Navratilova allowed to serve into the doubles alleys, while Connors played with no second serve, getting only one attempt per point. The opening set was closely contested, but Connors eventually secured a 7–5, 6–2 win. The event attracted close to 15,000 spectators and was considered a major entertainment spectacle, even though the result followed the expected script.

 

Karsten Braasch vs Serena and Venus Williams (1998)

 

At the 1998 Australian Open, the Williams sisters issued a casual challenge, claiming they could beat a male player ranked outside the top 200. Karsten Braasch, ranked near ATP No. 200 at the time, accepted the proposal in an informal, one-set exhibition. Braasch, who had reportedly spent the morning playing golf and arrived with a relaxed attitude, won both matches convincingly — 6–1 against Serena and 6–2 against Venus, played consecutively. While the matches carried no formal stakes, they triggered global discussion about the athletic and stylistic differences between the two tours, though the encounters themselves remained friendly and humorous in nature.

 

Andy Murray vs Serena Williams (proposed, 2019)

 

In 2019, a potential Serena Williams vs Andy Murray exhibition gained strong momentum in public discussion after Murray openly praised Serena’s achievements and hinted at interest in a mixed-gender exhibition. Both players exchanged playful remarks about the idea, which quickly captured fan imagination and generated widespread social media buzz. Despite the excitement, the match never advanced beyond informal talks, as tour commitments and scheduling limitations made the concept unrealistic at the time. Although it didn’t take place, the conversation reflected Serena’s continued pull in shaping tennis narratives beyond traditional competition.