Born in Merival, a rural village now located within the city limits of Ottawa, in 1867, Shillington was one of ten children of Thomas and Elizabeth Shillington. Shillington attended the Ottawa Model School and Collegiate. He then attended the University of Toronto, graduating in pharmacy.
He returned to Ottawa and opened a druggist business on Sparks Street. His business was successful and he invested in mining in the Haileybury area. He also became an executive with the Ottawa Hockey Club. In 1903, after the Ottawas had won their first Stanley Cup Canadian championship, he gave each player a silver nugget. That donation led to the nickname Silver Seven. He would manage the club through its 1903–1906 championship run.
- Kitchen, Paul (2008). Win, Tie or Wrangle. Manotick, Ontario: Penumbra Press. ISBN 9781897323465.
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