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For the Bill VS Discord, I fear that Death Battle will give Bill a W because of that soul reg thing. They have used soul reg to make Raven W.
Not if his powers are drained. When Bill's lost his power in the mindscape, Stanley literally just punches Bill's soul into oblivion.
So all Discord have to do is use Grogar's bell on Bill, drain his power and punch Bill's soul. Boom! Gone.
Discord's soul however will remain for as long as chaos are around to empower him.