With Spring Training approaching, Derek Jeter announced that the 2014 MLB season would be his last. He’ll play his 20th and final year with the New York Yankees, with whom he’s spent his entire career as a professional baseball player.

Along with winning five World Series championships, the shortstop has put up all-time great statistics. He holds the record for most ever hits and runs scored in the playoffs, in addition to recording over 3,300 hits in the regular season, However, as good as Jeter’s numbers are on the field, his prowess off it has been just as impressive.

Since he entered the Majors in 1996, Jeter has dated some of the biggest celebrities in Hollywood. Just as the Yankees began their dominant run in the late 1990’s, the future Hall of Famer entered into a relationship with singer Mariah Carey. The romance reportedly ended in 1998, but Jeter was only getting started.

Over the years, he’s been linked to the hottest young actresses in TV and movies. Scarlett Johansson, Jessica Biel, Jessica Alba and Jordana Brewster have all reportedly spent time dating Jeter. The Yankees star has also made the rounds with supermodels, Adriana Lima and Tyra Banks chief among them.

In recent years, Jeter has seemingly given up his playboy lifestyle and entered into serious relationships. Minka Kelly and Jeter appeared to be on the verge of getting married, but they split in 2012. Model Hannah Davis was Jeter’s latest girlfriend, but their breakup was reported just days before the MLB star announced his retirement.

After the recent split, rumors began to circulate why Jeter decided to end it with Davis. According to Page Six, Jeter has an issue with his girlfriends' fame.

“Derek likes to keep his relationships quiet,” a source told the New York Post. “In the past, when his girlfriends become famous and start doing sexy shoots, that’s when they break up. Exactly the same thing happened with Minka and Vanessa Minnillo.”

Jeter will be 40 years old at season’s end. It looks like he’ll begin his final year in the Majors without a girlfriend.