“Playing against my sister is that it’s like playing against myself,” Serena Williams once famously said, capturing the unique dynamic of their sibling rivalry. While Serena ultimately holds a 19-12 advantage in their head-to-head record, it was Venus who initially held the upper hand. Their first encounter came early in their careers, at the 1998 Australian Open, where Venus emerged victorious in the second round. Later that same year, Venus again defeated Serena in the quarterfinals of the Italian Open. But it was in 1999 that their rivalry truly began to capture the tennis world’s attention. That year, the two sisters found themselves facing each other in the final of the Miami Open—a match that, even 26 years later, continues to be lauded by tennis figures like Martina Navratilova and Danielle Collins.

By the time they reached their first final against each other, at the 1999 Miami Open, both Venus and Serena Williams were still teenagers—Venus, at 18, was a year older than her sister. Venus had already experienced the pressure of a Grand Slam final, having reached the US Open final two years prior. Serena, while yet to claim a singles major, had tasted Grand Slam success in mixed doubles, winning titles at both Wimbledon and the US Open with Max Mirnyi.

Serena entered their Miami final on a remarkable 16-match winning streak, a run that included her maiden professional singles titles at the Open Gaz de France and Indian Wells. Her elder sister was also in excellent form, having reached the quarterfinals of the Australian Open and successfully defended her title in Oklahoma.

Adding another layer to the occasion was their outspoken father, Richard Williams, who held a post-match press conference to declare, “This is what I have been planning for.” As the match began, he even held up a whiteboard with a message that read: “Welcome to the Williams show.”

Okay, so rewind to the 1998 Miami Open. Venus Williams was on a roll, having defeated the defending champion Martina Hingis in the semifinals. In the final, she faced Anna Kournikova. Despite dropping the first set, Venus rallied to win the next two, securing the title with a score of 2–6, 6–4, 6–1.

A year later, aiming to defend her title, Venus started strongly, securing the first set 6-1. However, Serena retaliated with her powerful groundstrokes, leveling the match by taking the second set 6-4. The final set was a closely contested affair, showcasing both sisters’ exceptional movement and Venus’ dominance at the net, ultimately leading to a 6-4 victory for the older Williams sister.

Fast forward over two and a half decades from that significant match, and marking 40 years since the Miami Open’s inception, it’s time for a celebration of tennis history!

On March 26th, Tennis TV shared the clip featuring Navratilova’s final against Chris Evert at the very first Miami Open, Novak Djokovic’s memorable doubles moment with his current coach, Andy Murray, from 2011, Roger Federer and Rafael Nadal’s first meeting at the 2004 edition, and Nick Kyrgios’ stunning tweener from 2019. While Iga Swiatek’s “OMG! So many great things happened in Miami” captured the video’s essence, it was the Williams sisters’ Miami Open memory that sparked the most heartfelt responses.

Danielle Collins, a self-professed admirer, once recalled the powerful message she learned from them: “It doesn’t matter where you come from, doesn’t matter your background, what you look like, how much money your parents have. If you set your mind to something and you work your tail off, anything’s possible.” Seeing footage of that first final, she exclaimed, “Two of my biggest childhood idols playing against each other.” Jessica Pegula also chimed in, noting the iconic outfits with beads that felt distinctly “Miami.”

Even Martina Navratilova, the inaugural Miami Open champion in 1985, was struck by the significance of that match, commenting, “First time they played against each other in a final and that was here too? Venus got the better of her younger sister that time…”

Madison Keys expressed her amazement that it was their first final encounter, adding, “I cannot imagine having to ever play my sibling. So props to them for the many many times that they’ve had to play.” The Miami Open founder, Butch Buchholz, simply stated, “Just two great athletes. They should be very proud.”

How many times have Venus and Serena Williams won the title here, though? Well, Venus Williams won the Miami Open thrice in her career (1998-1999, 2001) while her younger sister, Serena, has won this title eight times (2002-04, 2007-08, 2013-15), placing them among the 9 women to win multiple Miami Open titles. Now, since both these sisters have met each other so many times in their careers, which one, according to them, was their toughest battle?

Serena Williams reveals her toughest match against her elder sister Venus Williams

Serena Williams has won 23 Grand Slam titles in her career, whereas Venus has won just 7. They faced each other in nine Grand Slam singles finals, with Serena winning seven out of them. The elder sister won their first-ever major final at the 2001 US Open, but Serena won five consecutive Slam finals (2 at the Wimbledon Championships and one each at the other Grand Slam tournaments). But which among all these meetings in their careers was the most intense match?

According to Serena Williams, it was their 2003 Australian Open final where she defeated Venus by 7-6(4),3-6,6-4. Why, you ask?

“The most intense, for me the most mentally, was the Australian Open 2003. That final was so huge, as it was the first time I could win four Grand Slam titles in a row, which would be dubbed as a ‘Serena Slam.’ That was a tough match as she actually played really, really well and she should have won. I remember she missed a shot that she wouldn’t have missed in any other match, any other setting. I think I even looked at her across the side of the net, like: ‘How could you miss that.’…You have to think as an athlete, but it was tough,” she revealed in a past interview.

Serena Williams believes her sister Venus could have won a lot more Grand Slams had their careers not overlapped. “We had this rule that if we played against each other before the final, we had to win the title. I think Venus would have had a minimum of 15 Grand Slams if we didn’t play. I would have had 30,” said Serena at The New York Times’ DealBook Summit.

Despite the fierce competition on the court, Venus and Serena Williams always maintained a close bond, living together and supporting each other’s development as players. Looking ahead, it will be fascinating to see which memorable moment from the 2025 Miami Open earns its place alongside these iconic highlights in future celebrations of the tournament’s history.