The Keydets were coached by Duggar Baucom in his 4th year at VMI, and played their home games at Cameron Hall.

[1] VMI opened the year with an upset over the Kentucky Wildcats in Rupp Arena on November 14, 2008, by a score of 111–103.

After losses to Virginia and Jacksonville State to drop their record to 4–2, VMI then went on a ten-game winning streak and won their first six conference games before falling to Liberty 91–80, in what was the first sellout in the 27-year history of Cameron Hall.

[2] After finishing the regular season with a 22–7 mark, VMI cruised through their first two Big South tournament games, beating Coastal Carolina 96–76 in the quarterfinals and besting Liberty 78–58 in the semifinals.

The Keydets ultimately fell to Radford 108–94 in the Big South Championship game, ending their season at 24–8.