4. Jessica Biel

The 7th Heaven actress dated the Yankee superstar as the list was solidified even further. During the 2006 MLB season, the two dated for a short period of time.

Put it this way: Jessica Biel is downright gorgeous and is probably one of Jeter’s better accomplishments, on or off the field.

While she eventually went on to marry Justin Timberlake, Jeter got a commendable look at the Hollywood star.

 Next: Girlfriend No. 3