The VMI basketball program began in 1908 under head coach Pete Krebs, and team went 3–3 in their inaugural season.

Hired in 1958, Louis "Weenie" Miller became the first coach to lead VMI to an NCAA tournament appearance.

Despite being the 4th seed, VMI narrowly ran their way through the SoCon tournament defeating Furman, Davidson, and George Washington in succession.

[4] Bill Blair, who also played for VMI, led the Keydets to their first of what would be two consecutive NCAA tournament appearances.

After winning the SoCon tournament, VMI defeated Tennessee 81–75 and DePaul, 71–66 in overtime, before falling to Rutgers by a score of 91–75.

The team was led by Ron Carter, who went on to be the 26th overall pick selected by the Los Angeles Lakers in the 1978 NBA draft.

[5] Between 1978 and 2005, VMI had just three winning seasons between head coaches Marty Fletcher, Joe Cantafio, and Bart Bellairs.

Following the firing of Bellairs in 2005, VMI hired Duggar Baucom, a former Tusculum College head coach and North Carolina state trooper.

[4] That season was the first in which Baucom implemented a high-scoring, run-and-gun offense which garnered a considerable amount of notability.

The loss ended the Keydets' season at 24–8, which was tied for the second-highest single-season win total in VMI history.

The Keydets reached the Big South final once again in 2012, despite being the 7th seed, but fell to UNC Asheville 80–64.

It was the first season since the 2006–07 campaign that VMI did not lead the nation in scoring, ending a streak of five consecutive years.

VMI returned to their usual high-scoring pace in 2013–14, leading the nation in scoring averaging 88.3 points.

There were many notable performances in its time, including a trio of SoCon championships and Elite 8 and Sweet Sixteen VMI squads.