Wingo grew up in Greenwich, Connecticut and attended Old Greenwich School, Eastern Junior High School (now Eastern Middle School) and Greenwich High School. He attended Baylor University where he was a member of the Phi Delta Theta fraternity. Wingo graduated from Baylor University in 1985 with a bachelor’s degree in communications. Along with fellow ESPN broadcaster Matt Winer, Wingo previously worked at KSDK-TV in St. Louis, Missouri.