This depends on the cup and the sport. See related questions or re-ask your question.
The University of Toronto Varsity Blues (1909).
The New York Rangers
The Toronto Maple Leafs did not win the Stanley cup for the 2007-2008 season.
Montreal
What sport, what team, what cup? See related questions.
The Toronto Maple Leafs beat the New York Rangers to win their first Stanley Cup in 1932.
No, the Toronto Maple Leafs did not make the Stanley Cup Playoffs in 2011.
Yes.
George Armstrong was the captain of the last Toronto Maple Leaf team to win the Stanley Cup (1967).
The Toronto Arenas won one Stanley Cup in 1918.
Toronto arena's
The Stanley Cup was first presented to the Montreal Hockey Club in 1893.Though the Montreal AAA's were the first team to win the stanley cup this was back when the NHL did not exist and multiple leagues could contest for the cups.The first team to win the cup after the NHL was formed were the Toronto maple leafs (Toronto Arenas back then) in 1918The Torontos