Boon was the captain of the two-time Stanley Cup-winning Montreal HC teams of 1902 and 1903 which had several other future Hall of Famers including Jimmy Gardner, Tommy Phillips and Jack Marshall. He was effective despite being the smallest player on the team. Like many other members of the team dubbed the "Little Men of Iron", Boon left Montreal HC in December 1903 to found the Montreal Wanderers in the new Federal Amateur Hockey League (FAHL). He played with the club until 1905. At that point, professionalism was taking hold in hockey and Boon dropped out of playing hockey after the objections of his parents to him becoming a professional. He then turned to management of the Wanderers and he managed the club until 1916. He led the Wanderers to four Stanley Cup titles in 1906, 1907, 1908, and 1910 as Manager. Although Boon was a multiple winner of the Stanley Cup, he was not happy with it interfering in the season of play. In 1903, he was quoted as saying: "The Cup is far from beneficial to the game, it is detrimental."
