1957–58 Montreal Canadiens season

The 1957–58 Montreal Canadiens season was the club's 49th season of play. The Canadiens won their third-straight Stanley Cup and the tenth in club history.

Regular season

 * October 19, 1957 – Maurice Richard scored a goal at 15:52 of the first period. Richard became the first player to score 500 goals in a career.
 * Hockey's colour barrier was broken in Montreal. Midway through his second minor-league season with the Quebec Aces, Willie O'Ree was called up to the Boston Bruins of the NHL to replace an injured player. O'Ree made his NHL debut with the Bruins on January 18, 1958, against the Montreal Canadiens, becoming the first black player in league history.

Playoffs
In the semi-finals, Montreal played third place Detroit. After Detroit traded Ted Lindsay because of his union efforts, Detroit was a team in disarray. Montreal defeated the Red Wings in four straight games to reach the finals.

Stanley Cup Finals
Rocket Richard, was the top goal scorer during the playoffs with 11. In game five he notched his third final series overtime goal of his career and sixth playoff overtime goal of his career.

Boston Bruins vs. Montreal Canadiens Montreal won the best-of-seven series 4 games to 2.