After retiring from football, Stillie pursued a career in law and politics, and contested the 2019 UK general election as the Conservative candidate for the Central Ayrshire constituency.
Raised in Cumnock,[2] Stillie started his career as a youth player at Aberdeen and signed a professional contract in August 1995 at the age of 21; by that time he had already made his senior debut during the 1993–94 season due to an injury crisis.
He was an unused substitute as the Dons won the 1995–96 Scottish League Cup, but did not make any appearances that season with Theo Snelders and Michael Watt ahead of him; he remained a back-up as Nicky Walker came in as first choice for a short period, and then the veteran Jim Leighton took the place.
In July 2002, Stillie moved back to Scotland to sign for Fife club Dunfermline Athletic and became a virtual ever-present for the Pars, making a total of 117 appearances after replacing first-choice keeper Marco Ruitenbeek in November 2002.
[9] Having played more often for the Under-21s (14 appearances across two seasons)[10] than he had for Aberdeen at club level in the same period in the mid-1990s, Stillie was named in two senior Scotland national squads, latterly in October 2003, but never won a full cap;[11] he was an unused substitute in the Future Cup match versus Germany, also in 2003.