If you wanted just "Montreal" in general, before 1915 the Stanley Cup was the Challenge Cup and Montreal won it 19 times.
Also, in 1915-1916, 1923-1924 & 1925-1926 the Montreal Canadians were PCHA & WCHL/WHL champions
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The Chicago Blackhawks have won the Stanley Cup six times. They won in 1934, 1938, 1961, 2010, 2013 and most recently 2015.
The Pittsburgh Penguins won the Stanley Cup several times, the first being 1990-1991 followed by 1991-1991. Their third win came more recently in 2008-2009.