The team was established in 1888 playing local YMCA teams and fellow state teams without pads. Since then the Cavaliers have evolved into a multimillion dollar operation.

The Virginia Cavaliers' first team of helmetless young men in tight shirt, laced-up pants and high top cleats opened its season on a gravel strewn field, the historic contest witnessed by a meager gathering of fans and no press coverage. That 1888 squad of eleven men and one substitute played three games, winning two and losing one, on a five-acre tract behind what is now Madison Hall.

The first intercollegiate football game was played at UVA with the team dressed in Orange and blue school colors, that replaced the original red and gray. The General Athletic Association was formed to govern UVA sports in 1892, and Virginia joined its first league, the Southern Intercollegiate Athletic Association in 1894.

In between the years 1900-1915, Virginia change coaches 10 times and achieve 10 winning seasons with help from a quarterback named Robert K. Gooch and a Walter Camp All-American halfback named Eugene Mayer. The team joined the Atlantic Coast Conference on December 4, 1953.