I always thought the whole patriotic angle regarding cheering for a Canadian-based team solely because they're Canadian, and also because a Canadian team hasn't won since 1993 is pure BS. Especially when you consider that a good chunk of most NHL teams (never mind Canadian ones) are made up of non-Canadians. Hell, look at this season's Canucks team. Alternatively, if an American team has more Canadians on it than a Canadian team that made the final, which team should I cheer for? Which of the two would be deemed more patriotic?
My personal rule, which I've had since at least my early 20s if not earlier, is that I want my team to win the championship of whatever league they're playing in and every other team can go to Hell. I'm not going to cheer for the Edmonton Oilers because they're the only Canadian team left in the playoffs. I never cheered for them in the first place, dating back to when I was a child cheering for the original Winnipeg Jets. In a similar fashion, if the Winnipeg Blue Bombers were to get eliminated or didn't make the playoffs, I'm not going to all of a sudden cheer for another team, especially the Saskabush Cowtippers. NO! SCREW THEM! They can shove it up their combine harvesters if they don't like it.
When it comes to something like the Olympics, it's a different story. I'll gladly cheer for Canada in that instance, no matter the sport, but I'll also leave room to cheer on another team or athlete, particularly underdogs (think Latvia at last year's World Hockey Championships). When it comes to my favourite sports teams, on the other hand, it's my team or bust.