The Stanley Cup is a trophy awarded every year to the playoff champion of the National Hockey League. From 1917 to the end of the 2016 season, the trophy has been awarded 98 times. The Montreal Canadiens have won the Stanley Cup 24 times and made the finals another ten times. The Montreal Canadiens have won more cups than any other franchise. Trailing them are the Toronto Maple Leafs with 13, the Detroit Red Wings with 11, the Boston Bruins with 6 and Chicago Blackhawks with 6 as well. The Stanley Cup was not awarded in 1919 because of the Spanish flu epidemic and 2005 because of the NHL lockout. (List of Stanley Cup Champions)
As mentioned before the habs have won the Stanley Cup 24 times and here are the years in which they did so: 1915-16, 1923-24, 1929-30, 1930-31, 1943-44, 1945-46, 1952-53, 1955-56, 1956-57, 1957-58, 1958-59, 1959-60, 1964-65, 1965-66, 1967-68, 1968-69, 1970-71, 1972-73, 1975-76, 1976-77, 1977-78, 1978-79, 1985-86 and 1992-93. (Montreal Canadiens)
It's been 23 years since the Montreal Canadiens have won there last cup. I think they're due for another one!