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Armstrong turned pro at the end of the 1986-87 season with the Newmarket Saints. He played for them for three more seasons. The Leafs called him up for 11 games in 1988-89 and he scored 1 goal.
His daughter, Hannah Armstrong was part of Canada's National Women's Under-18 Team to a gold medal at the 2010 IIHF World Women’s Under-18 Championship in Chicago. As a member of the gold medal winning squad, a hockey card of her was featured in the Upper Deck 2010 World of Sports card series.