Born in either Calgary or Winnipeg, Gordon Dailley attended the University of Manitoba before moving to England in 1933 (reportedly working on a cattle boat to pay for his passage). In England, he joined the Grosvenor House Canadians (later the Wembley Canadians), playing defense, and later captained the Wembley Monarchs until World War II.

Dailley was part of the British team that won the gold medal in ice hockey at the 1936 Winter Olympics, despite controversy over player eligibility. He continued with the national team, becoming captain in 1937 and leading them to European Championships in 1937 and 1938 before joining the Canadian Army.

Dailley served in England throughout World War II. After the war, he stayed in the Canadian Forces, taking on various roles in Ottawa. He was part of the UN peacekeeping force in Korea and got promoted to colonel in 1955. From 1955 to 1960, he served as Canada's military attaché in Belgrade, Yugoslavia, and later became the base commander at CFB Gagetown in New Brunswick. Dailley retired from the military in 1964.