Woolford was surpassed by Charles Tillman for the most interceptions by a Bears cornerback, although Donnell achieved the goal 18 games faster than Tillman. He had 30 career interceptions four being with the Steelers and the rest with the Bears. He started every game of his career.
Upon retirement, Woolford returned to Fayetteville where he helped coach high school football. He later coached at East Lincoln High School in Denver, North Carolina. He was co-owner of the Fayetteville Ruff Riders football team from 2004-2005.
He was Clemson's legend representative at the 2014 ACC Championship Game. 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. Woolford is now associated with an auto warranty service and serves as president of the Donnell Woolford Foundation, assisting the Boys & Girls Clubs of America, and the Jimmy Raye Clinic in coaching local youth.
He donated land to build World Faith Ministries in Hope Mills, North Carolina, and continues to work in community activism as a board member of several non-profit organizations.