VMI

19th century

VMI football dates back to 1873 with a one-game season, featuring a 4–2 loss to Washington and Lee. No player or coaching records are known from that game. The Keydets would not have another intercollegiate team until 1891 under coach Walter Taylor III. Taylor was the son of Walter H. Taylor, a Civil War lieutenant colonel and aide to Robert E. Lee. The Keydets went 3–0–1 in 1891, with a win and tie against Washington and Lee and defeats of St. John's and Pantops Academy.

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.

1900–1920

VMI continued to have success on the field during the early 1900s. Sam Walker became the head coach at the turn of the century, and, after compiling a head coaching record of 11–7–3 in three seasons, was replaced by future College Football Hall of Famer William Roper. Roper's brief two-year tenure was highlighted by wins over NC State and Davidson.

After several seasons of mediocrity, VMI returned to their winning ways in 1911 under Alpha Brummage, who previously coached at now-NAIA Ottawa University in Ottawa, Kansas. In two years with Brummage, VMI went 14–2, and 7–1 each season, stumbling only to Virginia and St. John's, though VMI did manage to defeat and shutout the in-state rival and powerhouse Cavaliers 19–0 in 1912.

After Brummage left VMI for Kentucky, where he would become the school's football and basketball coach, the Keydets went 7–1–2 under new head coach Henry Poaque, his only season at the Institute. VMI joined the South Atlantic Intercollegiate Athletic Association (SAIAA) in 1918, many of the members of which formed the bulk of the Southern Conference after the conference's disbandment in 1921. In 1920, Blandy Clarkson led VMI to its third of only four perfect seasons with a 9–0 record, culminating with an SAIAA championship.

Alumni Field

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. The stadium was placed around the same place it is today, and was completed at a total cost of $69,000. 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.

Blandy Clarkson era

Following the perfect 9–0 championship season in 1920, VMI was much less successful the following year, posting a 3–5–1 record, which was the only losing season for the Keydets under Clarkson. After two stellar seasons of 7–2 and 9–1 as an independent, VMI joined the Southern Conference in 1924, where they would remain for nearly 80 years until 2003. In their inaugural SoCon season, VMI went 6–3–1, which was good for 13th place in a sizeable conference of 22. 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.

William Raftery era

Following the departure of Clarkson, Worcester, Massachusetts-native William "Bill" Raftery took over head coaching duties of VMI. The Keydets were 6–4 his first season, ranking among the last in the SoCon. Raftery led the team to an 8–2 season in 1929, but it was the last winning season under Raftery's reign, which lasted until 1936. In ten years his record at VMI was 38–55–5.

Allison Hubert era

Allison Hubert took over for his predecessor Raftery in the 1937 season. Nicknamed "Pooley", Hubert was a Mississippi native and a veteran of World War I. After leading Alabama to the 1926 national championship, Hubert coached several sports at Southern Miss in the early 1930s. He went 5–5 in his first season with the Keydets. Hubert's most successful season with VMI was in 1940, where the squad finished 7–2–1, though it was only good enough to get them 7th in the conference. Hubert left with a 43–45–8 record under his belt after ten seasons.

Tom Nugent era

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. Nugent was famous for developing the I formation, though it did not happen until the year after he left VMI. Though the first two years were nothing special, Nugent took the 1951 squad to their first SoCon championship with a 7–3 record. The season included a 34–0 shutout of Richmond, a 29–6 drubbing of Wofford, a 27–21 win over rival Citadel, and a 20–7 win over Virginia Tech in the season finale. Nugent left following the 1952 season.

Alumni Memorial Field and John McKenna era

Possibly the greatest decades in VMI football history were under John McKenna. In his thirteen years with the Keydets, McKenna had a record of 62–60–8, and won four SoCon championships. These occurred in 1957, 1959, 1960 and 1962.

In the same year VMI won the 1962 Southern Conference, 10,000-seat Alumni Memorial Field was built. Costs were around $250,000.

Bob Thalman era

Bob Thalman came to VMI in 1971. Coming from the University of Richmond, he previously coached at Hampden–Sydney. Thalman brought another two SoCon championships to VMI in 1974 and 1977. He departed in 1984 after a 1–9 season.

1985–2002

Eddie Williamson took over the head coaching position for four years, all losing seasons. He was followed by Jim Shuck, Bill Stewart, Ted Cain, and Cal McCombs until 2005. No coach could produce a winning season for the Keydets.

Big South and return to Southern Conference

In 2003, VMI joined the Big South Conference after 79 years in the SoCon. VMI still could not get back to its winning ways. They were under the direction of McCombs, who would be fired after 2005. Jim Reid would coach for two years, with a 3–19 record. Sparky Woods became the 30th head coach in 2008. The Keydets returned to the Southern Conference in 2014, but Woods was unable to lead a winning season; he was dismissed at the end of the 2014 season with a seven-year record of 17–62, and was replaced by Scott Wachenheim. The 2020 VMI Football team won the Southern Conference title with a 6-1 record, and a FCS Playoff berth. It is their first winning season since 1981.

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. By winning the SoCon Championship, The Keydets became an Automatic Qualifier for their first ever FCS Playoff berth. The following week, on April 24, The Keydets lost by one touchdown to the #1 ranked James Madison University Dukes, 31–24, in Harrisonburg, VA. Three members of the Spring 2021 Keydet Football team would eventually be selected as first-team All-Americans. Scott Wachenheim, Head Coach of the Keydets, would go on to win multiple collegiate coaching honors for the season including Southern Conference Coach of the Year and AFCA-FCS Coach of the Year. Wachenheim had led the spring 2021 Keydets to their first conference championship in over 40 years and their first ever FCS playoff bid. During the season, VMI was ranked amongst the Top 25 FCS Teams nationally for most of the season, rising as high as #10 in the FCS Stats Perform Poll and #11 in the AFCA Coaches Polls.