Bailey trains in Columbia, South Carolina under Curtis Frye and is the sister of the reggae star Capleton.

Bailey graduated from the University of South Carolina, where she competed during her Junior and Senior season after transferring from Barton County Community College.

In the 2003 NCAA Outdoor Track and Field Championships, Bailey won the 100 and 200 meters, both times defeating heavily favored Muna Lee of LSU.

At the 2005 World Championships in Athletics she won (together with Daniele Browning, Sherone Simpson and Veronica Campbell-Brown) a silver medal.

With this result, Jamaica qualified for the final, replacing Brooks and Bailey with Sherone Simpson and Kerron Stewart.