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Well, Bill killed Time Baby with a simple blast, Mind you Time Baby is already 4-D having total control over time, even able to make a Time wish, a wish that can alter time with no Paradoxes. Then having this with the fact that he literally ruined time, the fact that Time Baby said he would eventually destroy all things if he didn't stop and during Weirdmageddon he ruined Time and Space without even thinking about it, he was practically Omnipotent (To the Gravity Falls Universe) but had weaknesses that really didn't help him like being 'erased' by Stanly wiping his memory and unless the Lady of Pain wishes to lose her practical Nigh-Omniscience, he's not dying and that's saying he will make a deal with her too, which he most likely won't because she doesn't have anything he wants.
 
If you read the scan I posted from Die, Vecna! Die! (a D&D adventure from D&D 2nd edition), Lady of Pain can destroy the whole D&D multiverse (that is infinite in scope, and include even concepts such as good, evil, order, chaos, ideals, etc. —see Outer Planes in D&D lore for more info) only by revealing her true form.

I don't see why destroying time would give Bill more advantage in this battle.
 
I am going to go with Lady of Pain because of sheer feats Look I will be honest, I like bill more but his tiering is based on very likely guess work where as Lady of Pain has actually reworked/destroyed the multiverse.

The two are generally fairly similar and unlike most 2-A's like say, Nicol Bolas or Madoka, Bill doesnt really have any feats that put him at that level. Yes I am aware the novel says he could, but if we are going to argue via the novel, I could then also say higher dimensional beings fear bill and thus bill wins via higher tier.

Based on just what the two have done, I am going to go Lady of Pain high diff. I might change my vote to inconclusive later on depending on if someone corrects me, not that big on DnD.

Solid feats are just better then statements.
 
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