To answer the question of the last really good year for Canadian teams, you'd have to go back to good old 2003-2004.
5/6 Canadian teams qualified for the playoffs -- Edmonton only missed by three points or everyone would've been in. Toronto, Ottawa, and Vancouver all had over 100 points (back when that was more of an accomplishment and indicated you were definitely a contender). 3/5 Canadian teams advanced past the first round, with Calgary advancing all the way to the Stanley Cup final.
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