Donnell Woolford was born in Baltimore and attended high school at Douglas Byrd High School in Fayetteville, North Carolina. In high school, he was an avid athlete–three-sport star in football, basketball, and track. At Clemson he played for the Tigers from 1985 to 1988 at corner back. He was a first round draft choice of the Bears in 1989. He played for the Bears from 1989-1996 and finished out his career with the Pittsburgh Steelers in 1997. He was in the Pro Bowl in 1993 and was an All Pro in 1994. For interceptions he was in the top ten for 3 seasons. He had 111 interceptions for the Bears and 123 for his career. He had 101 tackles in 1993. Woolford was a cause for concern for quarterbacks on opposition. He is on the list of 100 Top Bears of All Time.
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