[1] He attended the University of North Carolina Greensboro, playing on the men's soccer team from 1988 to 1991.
In the spring of 1993, Gailey turned professional with the Greensboro Dynamo of the USISL.
[3] On November 5, 1993, Gailey signed with the Milwaukee Wave of the National Professional Soccer League.
[5] In 1995, Gailey joined the Tampa Bay Terror where he played for the next two NPSL seasons.
Gailey then spent the 1997–1998 indoor season with the Buffalo Blizzard before signing with the Charleston Battery in 1998.