He originally joined the Ottawa Senators for the 1898-99 season, when he scored 12 goals in 6 games. After a season with the Quebec Bulldogs, he rejoined Ottawa for the 1901-02 schedule. Stuart spent the next five years playing in the International League with teams such as Houghton, Pittsburgh and Portage Lake, before moving to the Montreal Wanderers. He assisted Montreal to the Stanley Cup in 1907-08 and then rejoined the Senators as their captain.
Bruce and the Senators immediately recaptured the Cup in 1908-09. After losing it the following season, Ottawas again crowned champion in 1911. Participating in three Stanley Cup victories, Stuart alone scored 17 goals in seven games. His best single game record against Quebec when he netted 6 tallies.
Stuart retired after the end of the 1911-12 season and will be remembered as an excellent all-around forward. Stuart was elected in the Hockey Hall of Fame in 1961. He had been battling health problems late in life, and died several weeks after his induction. He was 80.
For many years (1906 through 1952) he had operated a famous shoe store in his name on Bank Street in Ottawa, earning high praise in the business community. He was also a noted golfer and curler.