From Justine Henin to Angelique Kerber: Venus and Serena Williams open up on opponents who pushed them hardest

Venus and Serena Williams reunited for a new episode of their joint Stockton Podcast, revisiting the rivalries that shaped their legendary careers. The sisters discussed some of the toughest opponents they faced and reflected on pivotal matches that remain etched in tennis history. Venus particularly recalled her controversial match against Arantxa Sánchez Vicario at just 14 years old, a defeat that still resonates as a formative moment in her career.

Back in 1994, a duel took place that is still remembered decades later. A very young Venus Williams, just 14 years old—having already dazzled as a junior—made her professional debut, putting World No. 1 Arantxa Sánchez Vicario on the ropes. This moment was notably portrayed in the film King Richard, which chronicles the story of the Williams sisters' father guiding them through their early tennis years.

“I got iced in the film. So in this film, I end up winning my first-round match. I go pro at 14, win the first round. Then I'm playing the number one in the world, and I'm leading, like, 6-2, 3-1. I'm three games away from winning the whole match and beating the world number one,” Venus commented to her sister, recalling the controversial match.

“And she, like, takes a bathroom break. She definitely did not have to go to the bathroom. She was getting nervous,” Venus recalled. “She's like, 'This 14-year-old can't beat me.' And I knew what she was doing, and I couldn't stop it. I didn't have the mental strength to come back.”

The 7-time major champion acknowledged that even today she has regrets about the defeat in a match that seemed practically won. “I'm still mad at myself. She beat me once. I'm still mad about it, too. And I remember we were going home, and I was like, 'I shouldn't be going home.' I know I have to get stronger. I know that I was weak. And I knew that I had to build more character.”

On the other hand, the Williams sisters reflected on the rivals that complicated them the most during their careers. Serena began by acknowledging that her sister Venus was her toughest rival, although she ventured to mention some other great players of the era. “My toughest opponent besides Venus? Capriati was so hard. But that's in that era…” Serena began, referring to the American former No. 1 who retired in 2004. “I'll give different eras. I'd say Capriati. I'd say, for me, Justine Henin was hard.”

The 23-time Grand Slam champion acknowledged that she was challenged by two players with immensely different styles. While Capriati was characterized by a powerful game—which challenged even Serena's aggressiveness—Henin stood out for her variety and backhand, taking the rhythm of play away from Serena. Regardless, Serena led the head-to-head in both rivalries: 8-5 against Capriati and 8-6 against Henin.

Conversely, Venus's answers were surprising, mentioning that players like Henin or Capriati were not particularly difficult for her. “Definitely Davenport, Mary Pierce was hard to play for me. I didn't struggle against Capriati or Henin. Those were easier equations for me,” the 5-time Wimbledon champion said. “I think, like, Janković, Kerber... those matches were harder because I wasn't well. And they played long points. And it was tough for me.”