He served as head football coach at Virginia Union University from 1971 to 1983 and again from 1995 to 2003, Norfolk State University from 1984 to 1992, Saint Paul's College in Lawrenceville, Virginia from 2005 to 2010, and Virginia University of Lynchburg from 2011 to 2013, compiling a career college football head coaching record of 238–169–7.
As a coach in the Central Intercollegiate Athletic Association (CIAA), Bailey won seven conference championships, six with Virginia Union and one with Norfolk State.
These are players from Bailey's Virginia Union Panther, Norfolk State Spartan, and Saint Paul's Tiger teams who went on to the National Football League/Canadian League/Arena League: Bailey graduated from Norfolk State in 1962.
In 2021, he was inducted into the Black College Football Hall of Fame.
He is the president of Central International College, a religious-based school that opened in 2020, in Chester, Virginia.