Education
In 1988, Gailey graduated from Grimsley High School.
In 1988, Gailey graduated from Grimsley High School.
He played professionally in the National Soccer League and USISL.
He attende the University of North Carolina Greensboro, playing on the men’s soccer team from 1988 to 1991. He led the National Collegiate Athletic Association Division I in scoring in 1991. In the spring of 1993, Gailey turned professional with the Greensboro Dynamo of the USISL. He would play for the Dynamo for four summer seasons.
In 1993, he was a Sizzlin’ Six All Star.
On November 5, 1993, Gailey signed with the Milwaukee Wave of the National Soccer League. He was named to the NPSL All Rookie Third Team.
In 1995, Gailey joined the Tampa Bay Terror where he played for the next two NPSL seasons. In 1997, he played for the Seattle Sounders of the USISL A-League.
He was Second Team All League that season.
Gailey then spent the 1997-1998 indoor season with the Buffalo Blizzard before signing with the Charleston Battery in 1998. After nine games, he moved to the Raleigh Flyers. Gailey finished his career with the Atlanta Silverbacks in 1999.