Toronto Maple Leafs vs Montreal Canadiens

The Canadiens-Maple Leafs rivalry is the oldest and most storied in the NHL. Before the advent of separate conferences, they played in the Stanley Cup Finals five times, with the Maple Leafs taking three Cups at the Canadiens expense. They also claimed a third straight Cup in 1964, thanks in part to a thrilling win over Montreal in the semifinals in seven games. For a stretch, from 1956-1969, the cup was housed in either Toronto or Montreal every year but one. The debate about who was the more dominant franchise added to the rivalry as well. Since the late 1970s, the two clubs have not met in the playoffs, but because they play six times a year during the regular season, it s still hockey s best rivalry.