From 1956 to 2002, Wootten coached at DeMatha Catholic High School in Hyattsville, Maryland. He has the second most wins as a head coach in the history of basketball on any level, behind Robert Hughes. A number of his players went on to play in the NBA, including Adrian Dantley and Danny Ferry. Wootten gained legendary status in 1965, when his DeMatha team beat Lew Alcindor's Power Memorial Academy and ended their 71-game winning streak. His career coaching record stands at 1,274-192. As the head coach of DeMatha basketball, Wootten won 5 High School National Championships, 22 Washington, DC Championships, and 33 Washington Catholic Athletic Conference championships.

Former UCLA basketball coach John Wooden (1910–2010) described his admiration for Wootten when he said, "I know of no finer coach at any level – high school, college or pro. I stand in awe of him." On October 13, 2000, Coach Wootten was inducted into the Hall of Fame, one of three high school basketball coaches ever so honored. His overall record at the time was 1,210 wins and 183 losses.

This full size white panel basketball was signed in black by Wootten and includes a Great Moments COA.