During his first year in Morgantown, the 1993 West Virginia Mountaineers football team went undefeated and won the Big East Conference championship.

While at VMI He developed the Keydet defensive line into one of the best in the Southern Conference and guided two of his pupils to postseason recognition.

Bailey coached at the University of Louisiana at Lafayette for five seasons under three different head coaches—Nelson Stokley, Jerry Baldwin, and Rickey Bustle.

He improved a defensive line that had finished nearly last in every statistical category the year before, to the top three in sacks, tackles for loss, and quarterback hurries.

In 2005, Minnesota defeated Michigan for the first time in 19 years to recapture the Little Brown Jug given to the winner of the 100 plus year-old rivalry.

Another pupil of Bailey, defensive end William VanDeSteeg, led the Big Ten in sacks during the 2006 season (conference games).

In his first season, the Lamar defense produced its best performance since joining the Southland Conference, and two of Bailey's pupils garnered All-Conference recognition.

Bailey guided a defensive front in which the entire starting unit received all-conference recognition, highlighted by the second team selection of sophomore Omar Tebo.

Bailey also helped the Lamar defense set a school record for sacks, lead the Southland Conference in fumbles recovered and finish 11th nationally in turnovers gained.

In 2015, Bailey coached a defense that led the Southland conference in turnovers gained and finished third in tackles for loss.

In June 2012, Bailey was selected to participate in the Bill Walsh Fellowship program with the Atlanta Falcons of the National Football League (NFL).

In May 2015, Bailey was selected once again to participate in the Bill Walsh Fellowship program as a coaching intern, this time with the New York Giants.

Defensive ends Keionta Davis and Vantrell McMillan both earned first team all Southern Conference recognition.

Jackson, who came to Richmond as a safety, played his first full season as a defensive end for the Spiders and ranked seventh in the country in forced fumbles.

He was named the CAA Defensive Player of the Week for the final game of the regular season and earned his first career All America and All-Conference honor.

In January 2019, Bailey became the defensive line coach for the Toronto Argonauts of the Canadian Football League (CFL).

Defensive tackle Cleyon Laing was named an Eastern Conference All-Star and finished the 2019 season one sack shy of matching a career high despite missing three games due to a knee injury.