The Columbus Crew drafted Wingert in the second round (twelfth overall) in the 2004 MLS SuperDraft. Despite his collegiate success, MLS teams were skeptical about his ability to adapt to the faster and more physical professional game. Nevertheless, Wingert managed to earn a spot on a very good Crew team and was a versatile member of the squad for two years. While in Columbus, he played as both a defender and a defensive midfielder. On January 20, 2006, the Crew traded Wingert and Matt Jordan to the Colorado Rapids for a conditional and third-round draft pick in the 2007 MLS SuperDraft. On July 13, 2007, Real Salt Lake acquired Wingert from the Colorado Rapids for a first-round pick in the 2008 MLS SuperDraft and a second-round pick in the 2009 supplemental draft. After eight years with Real Salt Lake, Wingert was left unprotected for the 2014 MLS Expansion Draft and was selected on December 10, 2014, in the tenth round by expansion club New York City FC along with fellow Salt Lake teammate Ned Grabavoy.