[1][2] Woolford was a graduate of Douglas Byrd High School in Fayetteville, NC and Clemson University.

[7] He earned Pro Bowl honors in 1994 and was a three time All Madden Team Member during his career.

Woolford started every game for Chicago from 1989 to 1996, before being traded to the Pittsburgh Steelers, where he recorded 4 more interceptions, for a career total of 36.

He was co-owner of the Fayetteville Ruff Riders football team from 2004 to 2005[10] He was Clemson's legend representative at the 2014 ACC Championship Game.

[11] He was a graduate assistant coach with the Clemson national championship team in 2016, and was inducted into the South Carolina Hall of Fame in 2017.

[12] He donated land for the building of World Faith Ministries in Hope Mills, North Carolina, and continues to work in community activism as a board member on several non-profit organizations.