Dougary, an outside-left, was the son of one of the founders of Cowdenbeath football club.
He played for Lochgelly Amateurs and Moray House (where he trained to become a teacher) and for English side Stoke City during the First World War.
After the war, he worked as a teacher and began running schoolboy football matches.
The following year Cowdenbeath won the Scottish Second Division title, with a team largely put together by Dougary.
Dougary worked as a part-time scout for Liverpool, discovering Billy Liddell for the Anfield side.