Stingily began attending Joliet Junior College after graduating from Romeoville High School.

[1] On April 30, 2011, Stingily was selected by the Tennessee Titans in the sixth round, 175th overall, in the 2011 NFL draft.

Stingily was signed in order to fill in the vacant right tackle position after the Titans had released their former starter, Michael Oher.

[4] On October 19, 2015, Stingily was signed by the Pittsburgh Steelers to add depth to their left tackle position after Kelvin Beachum suffered a torn acl that would end the rest of his 2015 season.

He also has a younger brother named Cameron who previously played at running back for Northern Illinois University and was a member of the Pittsburgh Steelers.