With Mr. Phipp’s retirement in 1981, Dr. James Wilson became principal. Dr. Wilson oversaw the renovation of the school which modernized the library and added the business wing. Under Dr. Wilson’s leadership, the school’s reputation for academic excellence grew, as students became increasingly competitive in many areas. Woodson welcomed the addition of GT and AP classes to its curriculum and Woodson’s academic profile intensified. The results were reflected in 1984 when Woodson’s "It’s Academic" team made it to the All-Met finals and the math and English teams each took first place in the Superintendent’s Academic Competition. In the early 1980's WTW actually ranked first in the county due to its number of National Merit Scholars and outstanding test scores. Outside of class, Woodson students adopted the "Preppie" look in fashion so popular in the 80’s.

Charles E. "Chuck" Billak, who had been a biology teacher, WTW's first football coach, and an administrator, became principal in 1986. He led the school until his retirement in 1991.