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This boils down to Pokemon mechanics or Undertale mechanics. With Pokemon mechanics, Sans' attack can be considered pretty much any type I guess, so if one were to interpret them as Ghost, then they would destroy Shed immediately, otherwise I guess that Sans' attacks wouldn't do anything. However, with Undertale mechanics, not only does any hit do damage to anyone unless dodged, but Sans can attack outside of his turn. So I guess that since it's fought in the Judgement Hall, it's safe to assume that Undertale battle mechanics are used, so only straight-up attacks are allowed and Sans would win striaght-out.