Since the NHL added a franchise in Toronto in 1917, the rivalry between the two Canadian metropolises has never waned.  

The Canadiens and the Maple Leafs met in the postseason for the first time at the end of the inaugural NHL season, though it was the Blueshirts – as they were called since they had no official name yet – who came away victorious, eventually winning the Stanley Cup that same year.  Oddly enough, except on one occasion in 1925, the rivals didn’t face off against each other in the playoffs at all between 1918 and 1940. 

After meeting in the playoffs three times at the end of the 1940s, the rivalry between the two teams exploded in the mid-1950s. From 1956 to 1960, the Canadiens were the class of the NHL, winning a league record five consecutive Stanley Cups, the last two of which came against the Maple Leafs.   

After an anomalous season that saw the Blackhawks crowned champions in 1961, the Maple Leafs did their best impression of the Canadiens, hoisting the Cup in three consecutive years.  In 13 seasons, between 1956 and 1969, Montreal and Toronto combined for 12 of the 13 Stanley Cups that were handed out.  The Maple Leafs have not reached the Stanley Cup Finals since 1967, the longest drought of any team in the NHL. 

The Toronto-Montreal rivalry is only exacerbated by the fact that many of the superstars from both teams have switch over to the other side at some point in their careers, outraging the clubs’ most fervent and passionate fans. 

Since 1920, Sprague Cleghorn, Dick Duff, George Hainsworth, Frank Mahovlich, Dickie Moore, Bert Olmstead, Jacques Plante and Marcel Pronovost have traded in their bleu-blanc-rouge for the blue and white maple leaf and vice-versa.

In 1997, Ken Dryden, who backstopped the Canadiens to six Stanley Cup triumphs throughout the 1970s, accepted the position of president of the Maple Leafs. Dryden fought to bring Toronto into the North-East division to give the fans what they wanted to see: more Habs-Leafs games.