Barry began his footballing career in the Highland League with Ross County. He followed that with a brief spell at Southampton before returning to County in 1992 for a handful of games before moving to Raith Rovers. He spent almost 2 years with Raith and was a member of their squad that played in the UEFA Cup in season 1994-95. In 1996 Wilson then signed for Inverness Caledonian Thistle where he helped them to the Third Division title in 1996-97. He was sold to Livingston in 2000 and helped them gain promotion to the Scottish Premier League before he returned to Inverness Caledonian Thistle in 2003 where he spent a further 5 years before finishing his career with St Johnstone, Queen of the South, Peterhead and Elgin City.
Wilson holds Scottish First Division winner's medals, won with Caley Thistle, Livingston and Raith Rovers, a Scottish Third Division winner's medal, won with Caley Thistle and a Challenge Cup winner's medal, also won with Caley Thistle.
In July 2010 he became assistant Manager to Ross Jack at Elgin City and he has an SFA A-Licence coaching certificate.
Was appointed as Academy Manager on the 29th October 2012 and took the team to a 3rd place finish in his first season.