Twelve former VMI football players have risen to the professional ranks.The first was Bosh Pritchard "the Hopewell Hurricane" who played for the Philadelphia Eagles and New York Giants between the 1942 and 1951 seasons.

The three most recent VMI football alumni to play professionally were Mark Stock, two-time All-American Thomas Haskins (VMI’s all-time leading rusher) and Tim Maypray, who has enjoyed a standout rookie season in the CFL. Stock played wide receiver for Pittsburgh, Washington and Indianapolis between 1989 and 1996, while Haskins played five seasons with the Montreal Alouettes of the Canadian Football League and Maypray was signed by the Alouettes as well.

Bobby Ross, who captained the 1959 VMI football team, distinguished himself as a coach in both the collegiate and professional ranks, served as head coach of the San Diego Chargers and Detroit Lions, guiding the former to Super Bowl XXIX at the conclusion of the 1994. At the collegiate level, he coached The Citadel, University of Maryland, Army and Georgia Tech, winning a share of the 1990 national title at the latter.