Buenning played on both sides of the ball at Bay Port High School, earning all-state honors and committing to the University of Wisconsin.
[2] Playing at Wisconsin, Buenning was a four-year starter on the offensive line, and was a team captain his senior season.
[4] Buenning was selected by the Tampa Bay Buccaneers in the fourth round (107th overall) of the 2005 NFL draft,[5] and became an immediate starter.
[6] He played in nine games his sophomore season before suffering an anterior cruciate ligament tear against the Dallas Cowboys on Thanksgiving, sidelining him for the rest of 2006 and all of 2007.
[8] On September 2, 2008, Buenning was traded to the Chicago Bears for a conditional 2009 sixth-round pick.