He spent fourteen seasons of his professional career in Major League Soccer (MLS) with the Columbus Crew (2004–2005), Colorado Rapids (2006–2007), Real Salt Lake (2007–2014, 2016–2017) and New York City FC (2015–2016).

During his college years Wingert also played with the Brooklyn Knights in the USL Premier Development League.

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.

[4] Three days later, on February 2, he was claimed off of waivers by Real Salt Lake, starting his second stint with the club.