
Despite the record of athletic success in his family as well as a good youth career, Wingert was not highly recruited out of high school. Only a handful of colleges offered him more than an opportunity to try out for their teams. However, Dave Masur, head coach for St. John's University offered Wingert a full ride athletic scholarship which Wingert accepted. Wingert entered St. John's in 2000, beginning his collegiate soccer career as a midfielder. After his first season, Masur moved Wingert to defense where Wingert established himself as an exceptional collegiate player. During his four seasons at St. Johns, the Red Storm experienced considerable success, culminating in a trip to the 2003 NCAA Championship where St. Johns fell to Indiana. Wingert gained recognition as well. He was named both 2002 and 2003 first team All-American. He capped his collegiate career by winning the 2003 Hermann Trophy as the top college player of the year. Wingert played a total of 88 games for St. John's, missing only one game in his career, while playing for the US Under-23 team. In his four years at the university, he scored 13 goals and 12 assists.
As the U.S. began preparing for the 2004 Summer Olympic qualification tournament, the U.S. Soccer Federation (USSF) had asked Wingert if he would leave college early and turn professional. Wingert elected to play out his last season at St. John's and graduated in January 2004 with a bachelor's degree in communications.
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.