The 1943–44 Montreal Canadiens season was the club's 35th season, 27th in the National Hockey League (NHL). The team would win the Stanley Cup for the fifth time. Bill Durnan would join the club as its new goaltender and he won the Vezina Trophy in his rookie season.
In the Stanley Cup playoffs, Durnan allowed only 1.53 goals per game as the Canadiens skated to the title. At season’s end, Durnan was awarded the Vezina Trophy, the first rookie to win the award, and was selected to the league's First All-Star Team. 
Semi-final: Montreal vs. Toronto
Rocket Richard scored seven goals in the series, including all five for Montreal in game two. After giving up the first game at home to Toronto, Montreal took over, winning the next four, finishing the series with a 11–0 shellacking in game five.
Stanley Cup Final: Montreal vs. Chicago
Main article: 1944 Stanley Cup Finals
Maurice 'Rocket' Richard made his Stanley Cup debut with a five goal performance in the series, including a hat-trick in game two. The Punch Line of Richard, Elmer Lach and Toe Blake scored 10 of the Canadiens 16 goals. Blake scored the Cup winner in overtime. In the same overtime, Bill Durnan stopped the first penalty shot awarded in the finals, awarded to Virgil Johnson.