New York Yankees legend Derek Jeter had a charm spread all over the city of New York that was hard to resist for any woman. After all, there was a reason that people used to call the Bronx member a playboy during his bachelor days. Before Jeter got hitched to his now wife, Hannah Davis, he had his name linked to multiple women. Thus making his dating history even longer. But there was a catch. Almost every relationship he was in was kept under wraps as much as possible. It was because the Captain wanted to keep his personal life separate.

But somehow, the media caught the former shortstop either getting cozy with a woman or doing something simple with the woman he was getting linked to. Something similar happened when he got spotted with tennis star Anna Kournikova, who was already in a relationship with someone else. 

What was Derek Jeter doing with Anna Kournikova?

Notably, the Russian former tennis star and Hollywood actress Anna Kournikova is in a relationship with the Spanish singer and songwriter Enrique Iglesias. They’ve been together for more than two decades now. But at one point, Kournikova made headlines because of getting spotted with the New York favorite Derek Jeter. 

In 2004, while Enrique was on a tour in support of ‘7’, his girlfriend Anna Kournikova was spending time with the former shortstop. They appeared cozy at Miami’s Metro Kitchen + Bar in the Astor Hotel. According to Pop Dirt, “They arrived together and left together.” The source further added that although they were with a group of people, they sat next to each other, and another person said that they looked like a couple.

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The truth about that night is only known to Kournikova and Jeter. But it does not stop people from thinking that they might be together at the time. 

When did Derek start dating his now-wife, Hannah Davis?

Jeter met supermodel Hannah through mutual friends in 2012. They connected easily and started dating soon.

Watch this story: From Mariah Carey to Lara Dutta: Derek Jeter’s star-studded dating history

After three years of dating, Jeter popped the question, and Davis said yes. They got married the next year in 2016 and since have become parents to three beautiful daughters.