A complete list of Stanley Cup champions: 2016 -- Pittsburgh Penguins 2015 -- Chicago Blackhawks ... 1967 -- Toronto Maple Leafs 1966 -- Montreal Canadiens 1965 -- Montreal Canadiens Article content. The Conn Smythe era remains Toronto's best. The team's latest championship was in 1993. The Montreal Canadiens have won the Stanley Cup a record 24 times since 1915. He was best known for all his time spent in the penalty box. Dave "Tiger" Williams was one of the most charismatic players to ever play the game. Yet another Original Six franchise, the Toronto Maple Leafs have won the second most Stanley Cups in the league with 13. The Toronto Maple Leafs have played a total of 101 seasons. Including their cup wins under the names, the Toronto Pats and Toronto Arenas, the franchise has 13 Stanley Cups. George Armstrong, who played more games than any other Maple Leaf and was captain of their most recent four Stanley Cup teams, has died at age 90. This is a list of Stanley Cup Final appearances, which lists those teams that have played in the Stanley Cup Final series since the current play-off format was adopted in 1915.Before this, from 1894 to 1914, the Cup was won by challenge or league championship.Since 1927, the Stanley Cup Final series also determines the National Hockey League (NHL) championship. Their first season was in 1918, and their most recent season was in 2020. Most of its wins came during the years from 1956 to 1966 when it won five consecutive titles under coach Hector 'Toe' Blake. The senior-most team that has not won a Stanley Cup is the St. Louis Blues, who entered the league in the 1967-68 season. Tom Szczerbowski-USA TODAY Sports. Along with the Edmonton Oilers, the Penguins are tied for the most Stanley Cup championships among non-Original Six teams and sixth overall. It's pretty hard to get rid of their other streaks (no playoff wins since 2004, no Stanley Cup Final appearances or championships since 1967) when they can't get by Boston in Round 1. Overview. 41 Best: Tiger Williams. They haven't brought home a Cup since 1967… Kings of the Stanley Cup However, their most recent title came way back in the 1992-93 season. All are teams that joined the league since 1967. The absolute Stanley Cup champion team by number of wins is the Montreal Canadiens, which has won the title 24 times since 1893. The Blues showed promise early on, making the Stanley Cup finals in their first three seasons. The 1960s started and ended with one of the decade's hockey constants, a Montreal Canadiens Stanley Cup title. Here are the 15 best and the 15 worst Toronto Maple Leafs since their last Stanley Cup win in 1967. The team won cups in 1918, 1922, 1932, 1942, 1945, 1947, 1948, 1949, 1951, and under new majority ownership in 1962, 1963, 1964 and finally 1967. 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