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1. H2H
2. Can use standard weapons

Who wins how and why?

Didn't read the new Watchmen but going by the original comic I would give the edge to Night Owl, though tbh Rorschach is my most fav char in Watchmen. They should be roughly equals in skill in their Prime I though, but NightOwl is bigger and stronger. During the original Watchmen comic however I would give it to Rorschach because he never stopped and had the practice, while Night Owl already "retired".