After spending four years as an assistant at Miami University, Montgomery became the RedHawks' 32nd head coach succeeding Hoeppner, who became head coach at Indiana University. In his first year the RedHawks posted a 7–4 record including a tie for first place in the MAC East division. University of Akron won the tie breaker and represented the East in the MAC Championship Game. On November 29, 2008, Montgomery resigned as Head Coach of the RedHawks, after four seasons and a 17–31 record.