1915/16: The Canadiens rebound off a terrible season and finish in first place finishing with a solid 16-7-1 record. Representing the NHA the Canadiens faced the Portland Rosebuds from the PCHA with the Stanley Cup on the line. After the 2 teams split the first 4 games the Canadiens took the decisive 5th game when seldom used Goldie Prodgers found the back of the net in the 3rd period to give the Habs a 2-1 win for their first Stanley Cup. Players received $238 for winning the cup.

1955/56: With Toe Blake taking over the coaching reigns the Canadiens put together their first 100-point season finishing in first place with a 45-15-10 record, as Jacques Plante wins his first Vezina Trophy. In the playoffs the Hobs would turn it up a notch easily beating the New York Rangers in 5 games for their 6th straight Finals appearance. The Finals would end up becoming the Jean Beliveau show as the Canadiens star center scored 7 times as the Canadiens finally solved the Detroit Red Wings in 5 games. It was the Canadiens 8th Stanley Cup as they passed the Toronto Maple Leafs for most sips from Lord Stanley's Holy Grail.

1956/57: Coming off their Stanley Cup Championship the Canadiens finish in 2nd place with a solid 35-23-12 record. In the playoffs the Canadiens remained a super power beating the New York Rangers in 5 games. Facing the Boston Bruins in the finals the Canadiens received a boost right away as Maurice Richard netted 4 goals in Game 1, as the Habs jumped out to a 3-0 series lead. After being shutout in Game 4 the Canadiens buried the Bruins with a 5-1 in Game 5 for their 2nd straight Stanley Cup Championship.

1957/58: The Canadiens seeking their 3rdd straight Stanley Cup the Canadiens capture the regular season championship with a record of 43-17-10. In the playoffs the Habs remained hot as they swept the Detroit Red Wings in 4 games. Moving on to their 8th straight Finals appearance the Canadiens led by Maurice Richard win their 3rd straight Stanley Cup by beating the Boston Bruins in 6 games.

1958/59: The Canadiens remain the class of the NHL winning the regular season championship again with a record of 39-18-13. In the playoffs the Habs work past a stiff challenge to beat the Chicago Blackhawks in 6 games for their 9th finals appearance in a row. In the finals the Canadiens would win their 4th straight Stanley Cup despite Maurice Richard being held scoreless as they beat the Toronto Maple Leafs in 5 games.

1959/60: After breaking his nose Jacques Plante becomes the first goalie to wear a facemask in an NHL game on November 1st. With the mask in hand Plante would go on to win his 5th straight Vezina Trophy as the Canadiens finished with a league best 40-18-2 record. The Canadiens would sweep through the Chicago Blackhawks and Toto Maple Leafs on the way to their record 5th straight Stanley Cup. In the Finals Plante allowed just 5 goals in 4 games as Maurice Richard ended his career by netting his recorded 34th finals goal.

1975/76: The Canadiens rip through the NHL regular season finishing with best overall record and incredible 127 points with a 58-11-11 record. After a first round bye the Canadiens continued to dominate sweeping the Chicago Blackhawks in 4 straight. Moving on to the Wales Final the Habs won their first 3 games on the way to dispatching the New York Islanders in 5 games. In the Finals the Canadiens continued their dominant ways sweeping the Philadelphia Flyers in 4 straight. Despite the Habs dominance no one player could be singled out for the Conn Smythe as Flyers Reggie Leach took home the award.

1976/77: The Canadiens set new records in dominance as Steve Shutt scored 60 goals setting a record for Left Wingers. Helping to set Shutt up is Guy LaFleur who wins the Hart Trophy by amassing 1936 points a new franchise record. Along with LaFleur the Goalie combo of Ken Dryden and Bunny Larocque won the Vezina, as Larry Robinson took home the Norris during an incredible all-time NHL best record of 60-8-12 with an incredible 132 points. In the playoffs the Canadiens crushed the St. Louis Blues in 4 straights outscoring them 19-3 to advance to the Wales Final. In the Wales Final the Canadiens would fight off a challenge form the New York Islanders in 6 games. In the finals the Habs would easily beat the Boston Bruins in 4 straight as Guy LaFleur was named Conn Smythe. The victory gave the Canadiens their 2nd straight Stanley Cup Championship and their 20th overall, 7 more then the 2nd best.

1977/78: The Canadiens dominance continues as the only fall off slightly from their record setting year taking the best record again at 59-10-11, with 127 points. In the playoffs the Canadiens would continue to be untouchable as they clipped the Detroit Red Wings in 5 games.  Moving n to the Semi-Finals the Habs would sweep away the Toronto Maple Leafs in 4 straight outscoring them 16-6. In the Finals the Habs would suffer 2 straight losses as the Boston Bruins evened the series 2 games apiece. However, there would be no denying the Habs their 3rd straight Stanley Cup as the won the next 2 games by identical 4-1 scores as star defenseman Larry Robinson won the Conn Smythe trophy by setting up 17 Canadiens goals.

1978/79: The Canadiens continue to be one of the top team in the NHL winning the Norris Division with a solid 52-17-11 record. In the playoffs the Canadiens would be quickly mulch up the Toronto Maple Leafs in 4 games. Moving on to the Semi-Finals the Canadiens would be challenged for the first time in 4 years as they were pushed to a 7th game by the Boston Bruins. In Game 7 the Habs would advance to the finals with win a 5-4 win n overtime. In the finals the Canadiens would fall behind early losing Game 1 to the New York Rangers 4-1. However the Habs quickly grabbed back momentum with a 6-2 win in Game 2 on the way to winning their 4th straight Stanley Cup in 5 games. Bob Gainey the league's premier 2-way forward would earn the Conn Smythe award. Following the season the Ken Dryden, Jacques Lemaire and Yvan Cournoyer all announce their retirements, as Scotty Bowman resigns as head coach.

1992/93: In a season in which the hockey celebrated the 100th Anniversary of the dedication of the Stanley Cup the Canadiens put together another solid season with a 48-30-6 record. In the first round the Canadiens would get off to a slow start losing the first 2 games to the Quebec Nordiques, including an overtime loss in Game 1. As the series shifted to Montreal the Canadiens captured an overtime win of their own as they went on to win 4 straight to advance to the next round. In the Adams Division Finals the Canadiens stayed on a roll beating the Buffalo Sabres in 4 straight. However, it was not as easy as it seemed, as the Habs needed 3 overtime wins. Moving on to the Wales Conference Finals the Canadiens were paying their best hockey of the season winning 8 straight including 5 in overtime. In the Wales Conference Final the Habs continued to work overtime as they beat the New York Islanders in 5 games including 2 more overtime wins. Facing the Los Angeles Kings led by Wayne Gretzky in the Finals the Canadiens desperately needed to change the momentum as hey railed Game 2 at the Forum 2-1, as they faced a 0-2 deficit. Coach Jacques Demers decided to challenge the stick used by Kings Enforcer Marty MacSorley. His instinct were proven right as the curve was determined to be illegal setting up the Habs on the power play. The Canadiens would go onto tie the game forcing overtime where they won their record 8th straight playoff OT game. As the series shifted to Los Angeles the Habs continued their overtime magic taking 2 more games in extra time to establish a 3-1 series lead heading home. In Game 5 the Habs would not need overtime as Eric Desjardins record a hat trick in the Canadiens 4-1 win. The win gave the Canadiens their 24th Stanley Cup Championship, by far the most in the silver chalet's 100-yearhistory. Earning Conn Smythe honors for the 2nd time was Goalie Patrick Roy, who has a 2.13 GAA.