|Date of birth||February 22, 1984|
|Place of birth||Kingston, Jamaica|
|Height||5 ft 11 in (1.80 m)|
|Playing position||midfielder or striker|
|Current club||Portugal FC|
|Mercer County Community College|
1 Senior club appearances and goals
Bailey emigrated to the United States at the age of ten, settling in The Bronx. Bailey attended Mercer County Community College in 2002 and 2003, and was named an NJCAA first team All-American in 2002. Although he had a number of try-outs with European clubs, Bailey chose to sign with the MetroStars in 2005. He did not appear in a single league game for the club before being released in November 2005. In January 2006, he signed for the Finnish 1st division club Kokkolan Palloveikot (KPV). In November 2006, he played for KPV in the Suomen Cup Final against HJK Helsinki, which they lost 1-0.
Bailey has played with the Jamaican Under-17 and Under-20 national teams.