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Without looking, I would guess statistically speaking, Montreal would have the best odds, other than that it would depend on how well the Edmonton Oil Kings or Toronto St. Mike's or Marlboroughs were able to play back when the Oilers/Leafs were actually winning stuff.

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1969     
Memorial Cup:  Montreal Junior Canadiens

Stanley Cup:  Montreal Canadiens

 

1967

Memorial Cup:   Toronto Marlboros

Stanley Cup:  Toronto Maple Leafs

1964
Memorial Cup:   Toronto Marlboros

Stanley Cup:  Toronto Maple Leafs

1947     

Memorial Cup: Toronto St. Michael's Majors

Stanley Cup: Toronto Maple Leafs

   

1945   

Memorial Cup:  Toronto St. Michael's Majors

Stanley Cup: Toronto Maple Leafs

 

Edited by DSgamby
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1945 ans 1947 Toronto St Michaels Majors, Toronto Maple Leafs

1964 and 1967 Toronto Marlboros, Toronto Maple Leafs

1969 Montreal JR Canadiens, Montreal Canadiens

Crazy that all happened in a span of 24 years.

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