Most Stanley Cup championships

Montreal Canadiens (23): 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; 1992-93.

Toronto Maple Leafs (13): 1917-18; 1921-22; 1931-32; 1941-42; 1944-45; 1946-47; 1947-48; 1948-49; 1950-51; 1961-62; 1962-63; 1963-64; 1966-67.

Detroit Red Wings (11): 1935-36; 1936-37; 1942-43; 1949-50; 1951-52; 1953-54; 1954-55; 1996-97; 1997-98; 2001-02; 2007-08.

Boston Bruins (6): 1928-29; 1938-39; 1940-41; 1969-70; 1971-72; 2010-11.

Chicago Blackhawks (6): 1933-34; 1937-38; 1960-61; 2009-10; 2012-13; 2014-15.

Edmonton Oilers (5): 1983-84; 1984-85; 1986-87; 1987-88; 1989-90.

New York Islanders (4): 1979-80; 1980-81; 1981-82; 1982-83.

New York Rangers (4): 1927-28; 1932-33; 1939-40, 1993-1994.Ottawa Senators (4): 1919-20; 1920-21; 1922-23; 1926-27.