He ran his first competitive race at VPI. One of the West Point Black Knights' most celebrated distance runners, Dick Shea captured Heptagonal and IC4A individual cross country titles in three successive years (1949–51), helping Army to three straight team "Heps" titles during that time. The top performer on Army's dominant cross country team, Shea led the Black Knights to a 19–2 record during his West Point career, a mark that included three straight "shutouts" of arch-rival Navy.
At VPI, he ran in his first competitive race. Dick Shea, one of West Point's most celebrated distance runners, won Heptagonal and IC4A individual cross country titles consecutively from 1949 to 1951, aiding Army to three straight team "Heps" victories during that period. As the top performer on Army's dominant cross country squad, Shea led the Black Knights to a 19–2 record throughout his West Point career, including three successive wins over Navy.