Skillings attended Derry High School, where he practiced football and track.
Skillings accepted a football scholarship from Ohio State University, to play under head coach Woody Hayes.
Skillings was selected by the Dallas Cowboys in the sixth round (163rd overall) of the 1981 NFL draft.
[6] In 1983, he was limited while recovering from a broken ankle he suffered in the second preseason game against the Ottawa Rough Riders.
[10] In 2017, he was named a coach at United Senior High School in East Wheatfield Township, Indiana County, Pennsylvania.