He attended Bucknell University, playing on the men's soccer team from 2001 to 2004.

[1] In 2003 and 2004, he played for the Chesapeake Dragons of the Premier Development League during the collegiate off season.

On 4 February 2005, Real Salt Lake selected Lookingland in the second round (thirteenth overall) of the 2005 MLS Supplemental Draft.

He was named to the 2005–2006 All Rookie team and was the 2012 Major Indoor Soccer League Defender of the Year.

[2] On 4 April 2012, the Baltimore Bohemians hired Lookingland as an assistant coach.