The franchise known today as the Toronto Maple Leafs won the Cup in 1918 as the Toronto Hockey Club (later engraved on the Stanley Cup as the Toronto Arenas in 1947), and in 1922 as the Toronto St. Patricks. As of 2017, they have won 11 more as the Maple Leafs.
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Strictly speaking, Toronto has won more Stanley Cups, having won the Stanley Cup when it was a challenge cup before the formation of the NHL.
The Detroit Red Wings have won 13 Stanley Cups, while the number of Stanley Cups the Toronto Maple Leafs have won is disputed. They have won 11 Stanley Cups as the Maple Leafs, but also won 1 as the St. Patricks, and 1 as the Arenas before that, both precursors to the Maple Leafs. Before that, the Toronto Hockey Club won the Stanley Cup as a challenge cup.