Bailey was a three-sport athlete at Greeneville High School, playing soccer, basketball, and football.
[1] Bailey was selected to the Tennessee Olympic Development Program team and went on to be a starting keeper for the U.S.
[1] In 2017, he also played one season at City College of San Francisco, making 19 appearances and, as team Captain, won First-team All Conference accolades and made the All Western Region team, as recognized by the United Soccer Coaches Association.
[2][3] As well as college soccer, Bailey played in the USL PDL, appearing for Tri-Cities Otters in 2016,[4] and San Francisco City in 2017 and 2018.
[7] On February 9, 2024, Bailey signed with USL Championship side Memphis 901 ahead of their 2024 season.