Garry started his playing career with a youth team called Campsie Black Watch and at the age of 20 joined Scottish Second Division side Queens Park[1] as an amateur in which he spent two years before joining Kirkintilloch Roy Rob for a season where he headed to south west Scotland to semi-professional Scottish Second Division side Stranraer.

Gaining fifth place in the first season, Garry saw the team enter the play-off final for the Conference National at Stoke's Brittania Stadium, but lost to Altrincham.

In 2008, again Garry brought the team into the play-off final for a place in the Conference National and won 2–0 to Hampton & Richmond Borough at Stevenage.

After a difficult 2009/10 season Wilson managed to keep Eastbourne up on the final day by beating Oxford United 1–0 with an 84th-minute penalty from Simon Weatherstone.

Wilson was very close to leaving the job several times, including after the 4–1 home defeat to Tamworth, and it was rumoured that Steve King was ready to be his replacement.

"[10] On 17 February 2015 Wilson, his assistant manager Danny Bloor and first team coach Dean Lightwood departed Lewes by mutual consent.