Cup challenge with Edmonton Pitre jumped contract and went back to eastern Canada where he played with the Renfrew Creamery Kings in the FAHL for the remainder of the 1908–09 season. Montreal Canadiens Pitre joined the Montreal Canadiens in 1910 in the newly founded National Hockey Association (NHA), the clubs first season of existence, where he teamed up with Jack Laviolette and Edouard "Newsy" Lalonde. He initially stayed for four years with the Canadiens, before leaving for the west again. Pitre spent a year playing with the Vancouver Millionaires in the Pacific Coast Hockey Association (PCHA) in 1913–14, after having been lured over by Vancouver Millionaires owner Frank Patrick, in a coast-to-coast trade that saw Newsy Lalonde go the other way to the Canadiens. Pitre returned to the Montreal Canadiens the next year, in 1914–15. In 1916, Pitre led the NHA in regular season assists and points. He scored 24 goals, 15 assists (assists in those days were one per goal and only if the official scorer thought it contributed to the goal being scored) for 39 points. He also helped lead the Canadiens to their first ever Stanley Cup, defeating Portland Rosebuds of the PCHA over five games. He led the playoffs in goals as well. In the 1919 Stanley Cup playoffs, which were never completed due to the influenza epidemic, he led the playoffs in points. By 1921, the Montreal Canadiens had so much depth at forward, and an opening on defence due to the death of future Hall of Famer Joe Hall in the influenza epidemic, so they decided to try Pitre as a defenceman; not as difficult a transition as one might think, because he had previously been a rover during the days of "seven man" hockey. He remained with the Montreal Canadiens through the formation of the NHL and into 1923. A forward throughout his career, Pitre played the final two seasons as a defenceman. Playing style Didier Pitre's combination of speed, size and a hard shot made him one of the preeminent offensive players of his era. A forward and a right-handed shot, Pitre played predominantly on the right wing position, but he also figured occasionally on the old rover position before it was removed by the NHA in 1911–12. At times he was also used as a cover-point, and at the back end of his career with the Montreal Canadiens he would play