Question: when was the last time the toronto maple leafs won-stanley-cup
Answer: 1 -- 8 ) Punch Imlach 4 -- 1 Detroit Red Wings ( 16 , 7 -- 9 ) Sid Abel Eddie Shack ( 13 : 28 , third ) 1964 Toronto Maple Leafs ( 20 , 12 -- 8 ) Punch Imlach 4 -- 3 Detroit Red Wings ( 17 , 7 -- 10 ) Sid Abel Andy Bathgate ( 3 : 04 , first ) 1965 Montreal Canadiens ( 21 , 13 -- 7 ) Toe Blake 4 -- 3 Chicago Black Hawks ( 7 , 3 -- 4 ) Billy Reay Jean Beliveau ( 0 : 14 , first ) 1966 Montreal Canadiens ( 22 , 14 -- 7 ) Toe Blake 4 -- 2 Detroit Red Wings ( 18 , 7 -- 11 ) Sid Abel Henri Richard ( 2 : 20 , OT ) 1967 Toronto Maple Leafs ( 21 , 13 -- 8 ) Punch Imlach 4 -- 2 Montreal Canadiens ( 23 , 14 -- 8 ) Toe Blake Jim Pappin ( 19 : 24 , second ) 1968 Montreal Canadiens ( E ) ( 24 , 15 -- 8 ) Toe Blake 4 -- 0 St.