Iberico cheese in Winnipeg
I bought some Iberico cheese this summer, and I'm pretty sure it was from safeway, of all places, in their deli department. They carry manchego pretty regularly now, and both cheeses were of the same brand, which one I can't recall. I'll keep an eye out.
Failing that, you could try DeLuca's. They have cabrales and manchego for sure. La Grotta also has a pretty good cheese counter, as well as Fenton's at the forks.