The Toronto Maple Leafs and Boston Bruins are two of the oldest surviving franchises from the NHL’s first decade, yet somehow they have only met fifteen times in the playoffs over the past 94 seasons. A slim majority of the series have gone in Toronto’s favour, but that is all in our grandparents’ past, as the Maple Leafs have not beaten the Bruins in a playoff series since the 1950s. Expansion hurts us all. That and passing on Bobby Orr.
1932-33: Toronto Maple Leafs over Boston Bruins in five games - 3-2
The first time these two franchises faced off, the Maple Leafs took the five game semi-final series all the way to the limit, winning in game five.