1965–66 Montreal Canadiens season

The 1965–66 Montreal Canadiens season was the team's 57th season of play. The Canadiens won the Stanley Cup for the second consecutive season, and the 14th time in their history. Bobby Rousseau registered 78 points and tied with Stan Mikita for second in the overall 1965–66 NHL scoring race.

Finals
With this series, Toe Blake had coached the Canadiens to seven Stanley Cup championships in eleven years. Henri Richard, a member of all seven, would score the series winner in overtime of game six. Despite the Wings losing, their goalie Roger Crozier would win the Conn Smythe Trophy.

Detroit Red Wings vs. Montreal Canadiens

Montreal wins Stanley Cup four games to two.

Milestones

 * November 1965: Henri Richard got his 600th career point
 * January 1966: Richard would earn his 400th career assist
 * Jean Beliveau would play in his 800th career game during the season.
 * During the season, Beliveau would become the first Canadiens player to accumulate 500 career assists.

Draft picks
Montreal's draft picks at the 1965 NHL Amateur Draft held at the Queen Elizabeth Hotel in Montreal, Quebec.