5 Greatest Maple Leafs Seasons of All Time

5 Greatest Maple Leafs Seasons of All Time. Despite many believing that the NHL’s Original Six franchises all started at the same time, the Toronto Maple Leafs are actually the second-oldest active franchise in the league, with only the Montreal Canadiens having a longer history. Over the years, the Maple Leafs have had some incredible seasons, 13 of which have ended with the team hoisting the Stanley Cup.