Wilson is the son of Parker Wilson, a former professional baseball player for the Boston Red Sox organization. His mother Susan was a cheerleader for the University of Alabama. He is the younger brother of Alabama Crimson Tide quarterback John Parker Wilson, who currently plays professionally for the Atlanta Falcons.
Wilson played football and baseball at Hoover High School. In 2005, he quarterbacked the Bucs to the Super Six state championships. During the 2006 season, he was featured in the first season of MTV's Two-A-Days reality show, and the Bucs were the runners-up, losing to Prattville in the championship game. Wilson, a 3-year starter for the Bucs' baseball team, signed with the Alabama Crimson Tide baseball team.
At Alabama, Wilson in 2008 tied the single-season freshman home run record with 15, previously set by Jeremy Brown in 1999. During his sophomore season, he was a First-Team All-SEC selection and was named to SEC All-Defensive Team.
In 2010, after his junior year at Alabama, Wilson was drafted by the Chicago White Sox in the 10th round. He played his rookie season for the Great Falls Voyagers, where many of his teammates had watched the popular MTV show as teenagers. Wilson was nicknamed "Two-A-Days". Being in the White Sox organization gives Wilson the possibility of playing for the AA Birmingham Barons at Regions Park, where Two-A-Days was filmed, the home field of the Hoover Bucs football team, and the site of the SEC Baseball Tournament.
- Heffernan, Virginia (September 5, 2006) "Scrimmage Under the Sun, Brooding on the Sidelines." New York Times
- Stock, Erin (September 19, 2006) "Second season of MTV show possible". Birmingham News
- Stock, Erin (April 5, 2007) "Buzz subsides on MTV's 2nd season of 'Two-A-Days'". Birmingham News
- Rapoport, Ian R. (May 20, 2008) "Hoover's Ross Wilson hoping to add to list of memories at Regions Park". Birmingham News
- Estes, Gentry (June 8, 2010) "Ross Wilson to White Sox in 10th round; Jake Smith to Phillies in 15th". Mobile Press-Register
- Sumers, Brian (July 14, 2010) "TV fame for Hoover's Ross Wilson extends to Montana". Birmingham News