Brandon Holloway competed at Cooperstown Dreams Park with the Richmond Ravens (VA) during the week of August 8, 1998.

Brandon graduated from and played baseball at Clover Hill High School (Richmond, VA). He continued his education and baseball career at Bluefield College (Bluefield, VA) where he pitched and won the National Christian College Athletic Association Championship in 2009.

Upon completion of his collegiate career, Brandon was drafted in the 2009 Major League Baseball amateur draft by the Baltimore Orioles. He played professionally from 2009-2011.