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No team has managed the feat as often as the Habs, who have on four occasions raised the Cup with the same dejected opponent looking on in vain. Also the last team to have turned the trick, the Canadiens got the best of the Bruins in 1977 and 1978, their second and third of four straight championships in the late 1970s. 

Twice as Nice
The Canadiens have beaten the same team in the Stanley Cup Finals in consecutive years four times, more often than any other NHL team.
Canadiens def. Bruins	1977, 1978
Canadiens def. Blues	1968, 1969
Maple Leafs def. Wings	1963, 1964
Canadiens def. Leafs	1959, 1960
Canadiens def. Bruins	1957, 1958
Wings def. Canadiens	1954, 1955
Maple Leafs def. Wings	1948, 1949

Losing in consecutive Cup Finals to Montreal was a bit a tradition for the Bruins, who suffered the same fate in 1957 and 1958. The St. Louis Blues were swept back-to-back times by Montreal in 1968 and 1969, while the Maple Leafs were double-humbled by the Habs in both 1959 and 1960.

The Red Wings have done it once in their own right, victimizing the Canadiens in both 1954 and 1955. On the other hand, Detroit was handled by the Leafs in both 1963 and 1964, and 1948 and 1949.

Mike Babcock and Co. can take comfort in the fact that a team faced with the opportunity to eliminate a team for a second straight spring in the Finals has faired very well, posting a 7-2 mark.

The only teams to have accomplished what the Penguins hope to do are the 1984 Oilers, who beat the Islanders the second time around and the NY Rangers who turned the tables on the Leafs in 1933 after losing to Toronto the previous year. 

Manny Almela is a writer for canadiens.com