Youppi!, the Montreal Canadiens' official mascot, was the first character from a Canadian-based club to be inducted into The Mascot Hall of Fame. Having previously been the mascot of the Montreal Expos, Youppi! is also the first mascot to ever switch from Major League Baseball to the NHL. The terms of acquisition were reportedly in the six figures.

In the 1916 Stanley Cup Finals, the Canadiens defeated the Portland Rosebuds three games to two for their first Stanley Cup championship. It was the first time that a best-of-five Cup championship went the distance, and the Rosebuds were the first team based in the United States to play for the Cup.

On March 3, 1920, the Canadiens had a game for the ages. Four Canadiens players scored three or more times in the 16-3 drubbing of their provincial rivals, the Quebec Bulldogs. The 13-goal gap between the teams is still the largest margin of victory in franchise history.

In 2014-15, Carey Price finished the season as the leader of the three leading categories for goaltenders: GAA (1.96), save percentage (.933), and wins (44), all career highs. He would go on to win the Hart Memorial Trophy as the league's most valuable player, the Vezina Trophy as best goaltender, the Ted Lindsay Award as most valuable player as voted by the NHLPA, and the William M. Jennings Trophy for fewest goals allowed.

When the NHL was founded in 1917, Quebec did not operate a team its first season and the team's players were dispersed amongst the other teams. "Phantom Joe" Malone was claimed by the Canadiens. Playing on what was one of the most powerful forward lines of all time with Newsy Lalonde and Didier Pitre, Malone shifted to left wing and was the NHL's first scoring leader, registering 44 goals and 7 hat tricks in 20 games.

Known in his playing years as "Little M", as his older brother Frank was the "Big M", Pete Mahovlich won four Stanley Cup championships with the Canadiens. His best year came in 1974-75, when he racked up 82 assists and 117 points as part of a deep forward corps that included the likes of Guy Lafleur, Jacques Lemaire, Yvan Cournoyer, Steve Shutt and Bob Gainey.

On December 2, 1995, future Hall of Fame goalie Patrick Roy was left in goal for nine goals in a 12-1 home loss to the Detroit Red Wings. Believing he was left in after a five-goal first period solely to be taught a lesson in humility by head coach Mario Tremblay, Roy, once he was finally pulled, walked over to team president Ronald Corey and told him he had played his last game for the Habs. Four days later, Roy was traded to the Colorado Avalanche where he would win two Stanley Cups.

On October 1, 2018, Shea Weber was named the 30th captain of the Canadiens, replacing Pacioretty after he was traded to the Vegas Golden Knights. However, Weber did not join the Canadiens lineup until November 27 due to an injury during the offseason that required surgery. In his second game back, he scored two goals in a 5-2 win against the New York Rangers.

In 1981-82, Pierre Mondou made 35 goals on 146 shots for a franchise-record shooting percentage of 24%. Mondou won three Stanley Cups while with the Habs in 1977, 1978 and 1979. His career ended in 1985 when he was hit in the eye by a high stick from Ulf Samuelsson.

While playing for the Canadiens, Steve Shutt captured 5 Stanley Cups in 1973, 1976, 1977, 1978, and 1979. Shutt became the first left-winger in NHL history to score 60 goals in a single season, with the historic goal being scored on April 3, 1977 against the Washington Capitals.