In Montreal Ross attended Westmount Academy, and became active in a variety of sports, though he was best at hockey and Canadian football (which was still very similar to rugby football at the time). He likely first played organized hockey in the 1900–01 season, joining the Westmount Amateur Athletic Association. With this club he first met the brothers Lester and Frank Patrick, both of whom were later inducted into the Hockey Hall of Fame. Ross and Lester had a financially successful ticket resale business at the Montreal Arena, buying tickets for thirty-five cents and selling them for up to a dollar.