He has played in Major League Baseball (MLB) for the Oakland Athletics, Baltimore Orioles, Boston Red Sox, and San Diego Padres.

[3][4] Weeks was selected by the Milwaukee Brewers in the eighth round of the 2005 Major League Baseball draft, but he chose, instead, to attend the University of Miami.

Weeks was batting .297 in nineteen games for the Kane County Cougars in 2008 when a torn hip flexor ended his season.

At the start of the 2010 season, Weeks was ranked seventh in Oakland's farm system according to Baseball America[5] and appeared as a non-roster invitee for the Athletics in spring 2011.

On August 22, 2012, Weeks was demoted to the Triple-A's Sacramento River Cats when the A's activated outfielder Seth Smith and acquired Stephen Drew from the Arizona Diamondbacks.

[8] The Orioles traded Weeks and Iván DeJesús Jr. to the Boston Red Sox in exchange for Michael Almanzar and Kelly Johnson on August 30, 2014.

[9] On January 14, 2016, Weeks signed a minor league contract with the San Diego Padres that included an invitation to spring training.