How many times have the leafs won a standly cup?

Answer 1

10.

1921-22 season: (Then called the Toronto St. Patricks) lost in one-game NHL Finals by a score of 7-0.

1924-25: (Toronto St. Patricks) lost one-game finals 5-2 to the Montrael Canadiens.

1932-33: (called Toronto Maple Leafs) lost Finals series to the New York Rangers, 3-1.

1934-35: lost series to the Montrael Maroons, 3-0.

1935-36: lost series to the Detroit Red Wings, 3-1.

1937-38: lost series to the Chicago Black Hawks, 3-1. (not called Blackhawks until 1987)

1938-39: lost series to the Boston Bruins, 4-1.

1939-40: lost series to the New York Rangers, 4-2.

1958-59: lost in series to the Montreal Canadiens, 4-1.

1959-60: lost in series to the Montreal Canadiens, 4-0.

Answer 2

11 times

Answer 3

8 times.