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Teams

The most prestigious team award is the Stanley Cup, which is awarded to the league champion at the end of the Stanley Cup playoffs. The team that has the most points in the regular season is awarded the Presidents' Trophy.

The Montreal Canadiens are the most successful franchise in the league. Since the formation of the league in 1917, they have 25 NHL championships (three between 1917 and 1925 when the Stanley Cup was still contested in an interleague competition, twenty-two since 1926 after the Stanley Cup became the NHL's championship trophy). They also lead all teams with 24 Stanley Cup championships (one as an NHA team, twenty-three as an NHL team). Of the four major professional sports leagues in North America, the Montreal Canadiens are surpassed in the number of championships only by the New York Yankees of Major League Baseball, who have three more.

The longest streak of winning the Stanley Cup in consecutive years is five, held by the Montreal Canadiens from 1955–56 to 1959–60. The 1977 edition of the Montreal Canadiens, the second of four straight Stanley Cup champions, was named by ESPN as the second greatest sports team of all time.

The next most successful NHL franchise is the Toronto Maple Leafs with 13 Stanley Cup championships, most recently in 1967. The Detroit Red Wings, with 11 Stanley Cup championships, are the most successful American franchise.

The same trophy is reused every year for each of its awards. The Stanley Cup, much like its counterpart in the Canadian Football League (CFL), is unique in this aspect, as opposed to the Vince Lombardi Trophy, Larry O'Brien Trophy, and Commissioner's Trophy, which have new ones made every year for that year's champion. Despite only one trophy being used, the names of the teams winning and the players are engraved every year on the Stanley Cup. The same can also be said for the other trophies reissued every year.