For clever design I'm going to award this point to the Canadiens. The Penguins logo loses it because of the blatant hockey stick that penguin is holding.
Canadiens and Penguins both live in the arctic. But humans can be vicious and penguins are not and so's the way it goes.
In prior matches, I've talked about how cool the Canadiens logo is for working in that mysterious "H." Some will say it stands for "hockey" but I like to think there's something more behind it. Something French, perhaps so as to tie the logo to its home city of Montreal. Meanwhile, the Penguins logo has no connection to Pittsburgh and might as well be from Kansas City. And as for the logo itself, I was always more a fan of the '90s penguin.