Ramon Bailey (born February 22, 1984 in Kingston, Jamaica) is an Jamaican soccer midfielder and forward, who currently plays for the MetroStars of Major League Soccer.

Bailey emmigrated to the United States and The Bronx at the age of nine. While still in high school, he played with the Jamaican U-17 national team. Bailey then attended Mercer County Community College . He had a number of tryouts with European clubs, but chose to sign with the MetroStars in 2005.