However, he soon decided that he was too small, at just 5' 10" tall and 150 pounds, to play football in the Big Ten Conference.
He was then signed to play in the Arena Football League by Mike Hohensee, then-head coach of the Albany Firebirds.
On November 17, it was announced that Stingley had signed with the Bossier-Shreveport Battle Wings to become the team's defensive coordinator.
On October 15, 2008, the VooDoo announced that the team was ceasing operations resulting in Stingley's contract being nullified.
[11] Stingley was announced as the first head coach of the Shanghai Skywalkers of the China Arena Football League (CAFL) in June 2016.
During the CAFL hiatus, he was also the head coach of the Georgia Doom of the American Arena League (AAL) for four games in 2018.
[15] He currently resides in Baton Rouge, Louisiana along with his wife Natasha and their four children Isis, Nahjha, Derek Jr., and Sanaa.