I've had the pleasure of listening to the same debate at a well known "southern Ontario" university. It came down to pretty much a somewhat racist approach to sports. "I'm Canadian, so I cheer for the leafs" how that makes any sense is beyond me, but it is interesting.
I myself am Canadian, born and raised in northern Ontario, There are photos of me around 2-3 years old with an oilers jersey. Why? I have no idea. My mother says it was because it was in the early Gretzky era and the jerseys were abundant n cheap. A few years later i got my first habs jersey. Why? I have no idea. But I've been a proud habs fan ever since. What boggles my mind the most is my mother hates hockey, and my father is a leafs fan.
To say all Canadians have to cheer for Toronto, or any Canadian team for that matter is narrow minded. Plain and simple. I guess that comes from a Toronto is the be all and end all of Canada state of mind. Have fun down there.
It's a game, quit over analyzing it and enjoy it for what it is.... a game.