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Ranking Derek Jeter Girlfriends Over The Years

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Ranking Derek Jeter Girlfriends Over The Years

Ranking Derek Jeter Girlfriends Over The Years
Kim Klement - USATODAY Sports

An ankle injury may be keeping New York Yankees shortstop Derek Jeter off the field until at least the Major League Baseball all-star break this season, but there has been nothing that has been able to keep Jeter off the dating circuit all these years.

Since he’s not able to make news with his play on the field this season, there has to be a way for Jeter to stay in the news. Now is the perfect time to examine all the news Jeter has made in tabloid gossip columns during his time as a Yankee. The Yankee captain has more ex-girlfriends than he does World Series rings during his career, as he has taken full advantage of the fact that he lives in New York City where he is one of the most eligible bachelors.

It’s been difficult to keep up with who Jeter has and hasn’t dated, so we have come up with a list of the top 10 girlfriends he has had over the years. Just cutting the list down to a top 10 was quite a challenge, as there is an almost endless list of attractive and famous women that Jeter has been romantically linked to, or rumored to be linked to, during his time in New York. But even once the top 10 was established, finding a way to order them was even more difficult.

The process was quite subjective, so feel free to disagree, but it was put together using a combination of attractiveness, fame, and compatibility with Jeter. So without further ado, here are Jeter’s top 10 girlfriends.

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10. Mariah Carey

10. Mariah Carey
Sgt. Michael Connors

Dating Mariah doesn’t seem all that impressive now, but she and Jeter were an item back in the mid 90s when she was at the top of her game and Jeter was still ascending. Even then it didn’t seem like a couple that made a lot of sense, but Jeter had to have been a fan of Mariah during his teen years. Fulfilling that fantasy must have been nice for the 1996 Rookie of the Year.

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9. Lara Dutta

9. Lara Dutta

She was once Miss Universe and Jeter for many years was an all-Universe shortstop, so that makes some sense. However, what would a Yankee and a Bollywood star really have in common? Although it was probably a nice relationship while it lasted.

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8. Gabrielle Union

Gina Hughes

Gabrielle was great at playing a cheerleader in “Bring It On”, but baseball isn’t a sport that has cheerleaders so these two aren’t a great match. But she is young and pretty, so it’s safe to assume that’s Jeter’s type.

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7. Jordana Brewster

Andre Luis

She was a former soap opera star, and just like baseball, soaps are on every day so it made sense for these two to get together. Brewster is pretty and has been in some big movies, but she can’t match Jeter’s level of success so the relationship didn’t last too long.

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6. Jessica Biel

6. Jessica Biel
Chris Rodal

The relationship between Jeter and Jessica lasted a year which is a big deal as both of them are known for dating a lot of people. Jessica is pretty, but Jeter has done better which we’ll find out as we move forward on the list.

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5. Tyra Banks

David Shankbone

She’s not the supermodel she used to be, but having a fling with Tyra is still a big deal, even for someone with the dating history of Jeter.

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4. Vida Guerra


Jeter and Guerra had nothing more than a brief fling, but there’s nothing wrong with that when it comes to two extraordinarily attractive people. The lack of sustained relationship keeps Guerra a little lower on this list than she should be, but she is definitely on of the best looking ladies on Jeter’s list of exes.

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3. Adriana Lima

3. Adriana Lima
Snob Models

The courtship was brief, and apparently PG, but there’s nothing wrong with walking hand in hand with a supermodel and one of the most beautiful women in the world. Jeter is an elite athlete and Adriana is an elite model, so it made sense for them to cross paths at some point.

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2. Minka Kelly

2. Minka Kelly
Eva Rinaldi

This was Jeter’s longest relationship and, reportedly, she almost got him to walk down the aisle with her. Jeter may never settle down so Minka scores major points for coming the closest to settling down with the Yankee captain. She also gets major points for being beautiful.

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1. Jessica Alba

Flickr - miguel77

Honestly, is there anything better than dating Jessica Alba? Supermodels are great and all, but there are few women on the planet that can top the fame, beauty, and talent of Alba. However brief the courtship was between her and Jeter, it’ll be tough for Derek to top her no matter how many ex-girlfriends he accumulates with the rest of his days.