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.

Regular season

Final standings

Record vs. opponents

Schedule and results

Playoffs

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.

Player statistics

Regular season

Scoring

Goaltending

Playoffs

Scoring

Goaltending

Milestones

Draft picks

Montreal's draft picks at the 1965 NHL amateur draft held at the Queen Elizabeth Hotel in Montreal.