Dutton attended school at St. John's College in Winnipeg. He left school in 1915 to volunteer with the Canadian Expeditionary Force (CEF) in World War I and served with the Princess Patricia's Canadian Light Infantry. He lied about his birth date on his CEF enlistment papers as he was not yet 18, and served for four years. Dutton fought in the Battle of Vimy Ridge in 1917 where he suffered a shrapnel wound to his leg serious enough that doctors pressed for amputation. Dutton refused and spent the following 18 months working to recover full use of his leg. He played hockey almost constantly to regain strength, at one point playing in seven different Winnipeg leagues at the same time.