VMI football dates back to 1873 with a one-game season, featuring a 4–2 loss to Washington and Lee.

VMI had two additional undefeated seasons in 1892 and 1894, and a total record of 32–10–2 during the 19th century, setting the tone as being one of the state's top football schools.

Although they were technically undefeated in 1899 by a virtue of a lone win over Washington & Lee, the season was cut short and all cadets were sent home due to an outbreak of typhoid fever.

In 1920, Blandy Clarkson led VMI to its third of only four perfect seasons with a 9–0 record, culminating with an SAIAA championship.

With the finished construction of Alumni Field in 1921, VMI football no longer needed to play on the Parade Ground situated in front of the barracks.

[6] The Keydets went 3–5–1 in the stadium's inaugural year, which included key wins over in-state opponents Roanoke, Hampden–Sydney, and a stunning victory over Virginia.

[7] Clarkson departed VMI following the 1926 season, and totaled a record of 44–21–2 in seven years, the most wins by any Keydet head coach at the time.

Following the departure of Clarkson, Worcester, Massachusetts-native William "Bill" Raftery took over head coaching duties of VMI.

After leading Alabama to the 1926 national championship, Hubert coached several sports at Southern Miss in the early 1930s.

When Arthur Morton left VMI for Mississippi State in 1949, he was 9–8–1 with the Keydets.Tom Nugent took his place that January.

In the same year VMI won the 1962 Southern Conference, 10,000-seat Alumni Memorial Field was built.

The 2020 VMI Football team won the Southern Conference title with a 6-1 record, and a FCS Playoff berth.

During the 2021 FCS spring season, VMI defeated The Citadel 31–17 in the Military Classic of the South, retaining the Silver Shako, and winning their first Southern Conference Football Championship since 1977.

Wachenheim had led the spring 2021 Keydets to their first conference championship in over 40 years and their first ever FCS playoff bid.

The stadium went through a major $12 million renovation process in 2006, with new ticket booths, concourses, restrooms, and a new scoreboard and jumbotron.

[11] Originally the kangaroo was named TD Bound, but later changed to Moe at an unknown time.

Around 20 minutes before VMI home games, the Corps of Cadets march from their barracks down to Foster Stadium while the regimental band plays.

VMI uniquely requires every student to attend the football games from start to finish.

Arguably the school's biggest rival, The Citadel and VMI have played 76 times in a matchup known as the Military Classic of the South.

[3] The most recent meeting occurred in 2021, when VMI prevailed 31-17, their second consecutive win in the Military Classic of the South.

Virginia Tech and VMI first met in 1894 and played annually from 1913–71, usually in Roanoke on Thanksgiving Day.

Due to the long pause of the VMI-VPI series, the Virginia–Virginia Tech rivalry has emerged as the dominant one in the state.

However, in 2017, Virginia Tech and VMI agreed to a one-time rivalry matchup on September 5, 2026 at Lane Stadium.