Derek Jeter—the Captain and the New York Yankees legend—owns a career packed with numerous milestones and moments. Across his 20 years of building a Hall of Fame career with the Yankees, he has earned many titles on the field. However, off the field, he had another title attached to his name: the most eligible and relentlessly pursued bachelor.

The former star shortstop is now happily married to Sports Illustrated swimsuit model Hannah Davis. They tied the knot in 2016, and since then, they’ve welcomed four children into their lives. However, it has been an intriguing journey for Jeter to get there.

Formally being one of baseball’s most celebrated bachelors, he was romantically linked to many A-listers throughout his years in the Bronx. Only a few of his relationships were confirmed publicly. Apart from those, Jeter was also rumored to be dating many models and Hollywood stars. Let’s take a tour through Jeter’s most talked-about romantic relationships.

How many people did Derek Jeter date? A look at them

Derek Jeter has been off the dating market since 2016. It’s been a while, and as he turns 51, it’s worth revisiting his dating timeline. In all honesty, nobody would know the exact number of women he was romantically involved with other than the shortstop alone. However, his romantic life hasn’t all been behind the curtains. As we do know, quite a few of the women he’s been linked to across these two decades and more.

Before fate introduced Jeter to his now-wife, Hannah, he had dated women who tended to be models and actresses, actively in the public eye. Uh oh, the list is going to be long. Let’s begin, shall we?

Jeter’s first girlfriend from the industry was Mariah Carey. He and Carey were together for barely a year (1997-1998). It was around the end of her marriage to Tommy Mottola. It turns out Jeter helped her get out of her toxic married life with Mattola.

Next up, we have Adriana Lima. Yes, the Brazilian model who also starred in ‘How I Met Your Mother.’ Then, during the early 2000s, Jeter was linked to Tyra Banks. However, reports never confirmed their relationship. There was another name that surfaced around the same time. It’s none other than Gabrielle Union. However, Union shut down the dating rumors some years later, saying, “If I were dating Derek Jeter, trust me, I’d announce it to the world.”

Hold on, the list is still long…

Joy Enriquez also dated Mr. Clean in 2001. In fact, she attended his games as well. During that year, these two were often spotted together.

Scarlett Johansson is next on the list. She was supposedly linked to Jeter in 2004. However, she denied it some time later, stating that she was not involved with him in any way. Jeter then dated Vanessa Lachey from 2003 to 2006. For three years, they were mostly on and off. This was likely because, in 2004, during the early internet era, Jeter was dating Jessica Alba.

Later in 2005, Jeter was romantically involved with Vida Guerra. For the record, Guerra also congratulated Jeter when he married Hannah. In 2006, Jessica Biel was in the picture. They didn’t date for long, as sometime later. Biel announced her marriage to Justin Timberlake.

Next up, it’s Indian actress Lara Dutta. The former Miss Universe dated Mr. Clean in the early 200os. Some other rumored girlfriends are Jordana Brewster, Rachel Uchitel, and Bridget Hall.

Lastly, it’s Minka Kelly. She was Jeter’s most talked-about love affair before getting married to Hannah. He dated Kelly from 2008 to 2011. Then, his dating era came to an end, as in 2012, he finally met the love of his life—Hannah Davis, who is now Hannah Jeter.

Most talked about love affair: Derek Jeter and Mariah Carey

Vividly, around the late 90s, Mariah Carey and Derek Jeter were doing pretty well in their respective fields. These two were the talk of the town for a whole year, 1997 to 1998. However, while dating Jeter, Carey was still legally Tommy Mottola’s wife.

In a 2020 interview, Carey herself credited Jeter for helping her get out of her toxic marriage. She emphasized that Jeter was a turning point in her life. Her famous songs ‘The Roof‘ and ‘My All‘ were both dedicated to the Yankees legend. That’s a reflection of how much this relationship meant to Carey.

That year, 1996, Jeter won the Rookie of the Year and also notched the World Series title. Unfortunately, they broke up in 1998; however, it seems this relationship had a lasting impact on Carey. And, well, maybe for Jeter too.

A rumor that never materialized: Inside Derek Jeter and Minka Kelly’s marriage speculations

Well, right before Hannah came into Jeter’s life, he was rumored to be privately engaged to supermodel Minka Kelly. He began dating Kelly in 2008, and after that, the two were frequently spotted in the city. After one year of dating, fans started speculating about these two getting married.

After this rumor, they were spotted together even more frequently. Fans started ‘shipping’ the two and believed the wedding buzz. Minka was also spotted with Jeter at the Empire Hotel. After that appearance, she later denied being in a relationship with him.

“There is no fall wedding planned with Derek Jeter,” Minka’s representative also clarified. For the record, Jeter has always been well known for keeping his life private. He has always been silent on all dating rumors, even when, at times, his ex-partners have been vocal.

The two mutually broke up in 2011, and it stunned the baseball world and beyond. The rumored engagement was never officially confirmed, but fans already believed it well. Jeter’s relationship with Minka was arguably one of his most remembered off-field chapters.

A meeting that changed everything: All about Hannah and Derek Jeter’s relationship timeline

After Derek Jeter’s relationship with Minka came to an end in 2011, the Bronx star was single once again. Well, let’s just say the universe had a better plan for him.

One fine day, he was out with his friends in the city. They all went to a restaurant, and that’s where Jeter met Hannah Davis, the Sports Illustrated model who was there for a dinner date with her mom. Hannah was introduced to Jeter via a mutual friend. Guess what? His now-wife had no idea who ‘Derek Jeter’ was back then.

In August of the same year, Jeter and Hannah were spotted at a club in the city. They were spotted together but left separately.

They were extremely private about their outings. Soon, fans started speculating about their engagement, and in 2015, it all came true. It’s like the fans manifested this pair. In a blog post, Jeter referred to Hannah as his “fiancée.” Then, sometime later, the couple made their red carpet debut at the Met Gala. They also posed together that day.

In November, at the CMA awards, Hannah also showed off her engagement ring. Finally, in 2016, the couple had a beautiful July wedding at Meadowood Napa Valley in California. It was an intimate wedding with just family and friends. Well, that was Jeter’s happily ever after. Now, these two have created a beautiful life in Miami as they curate memories with their kids.