The Toronto Maple Leafs were the last team to win the Stanley Cup during the Original Six era in 1967, their 11th championship overall. Since then, the Leafs have struggled mightily to get back to the final, despite making four conference final appearances. Their 54-season Stanley Cup drought (and counting) is the longest in NHL history. Maple Leafs fans have endured a lot of heartbreak over the past half century-plus as the team aims to end Canada’s 29-year Cup championship drought.
