who wins this fight?
The Lady's overall capacity is kind of nebulous to really be able to say much here. I mean, I don't know that anything by contrast suggests Sauron could resist BFR to the Mazes, but still.
My knowledge of old tabletop campaigns is a bit spotty. But to my knowledge the only person to ever resist the Lady of Pain was the most powerful wizard in the universe during his bid for total multiversal conquest; in which he did things like devour a god, escape the inescapable prison dimension, defy the will of the Lady of Pain, and break the universe so hard that the rules of reality had to be completely rewritten to cover the damage.
The Lady of Pain is such that D&D major powers don't muck around with Sigil, and these are beings who would trivially solo Third Age Middle Earth.
Lady of Pain has no stats in the stat book. Meaning you cannot kill her.
And as mentioned she keeps big names away from Sigil, her city and said names can defeat the Third Age Middle Earth.
Which is pretty crazy in itself.
Considering I think a party of D&D characters at high enough level with right gear could kill Sauron (Chop ring finger off) That goes without saying.
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And I gotta say the Lady sounds like she could easily handle Sauron. Sharp, I'm going to put words in his mouth.....hope he ain't mad, would probably note that Finrod was able to at the very least contend with Sauron in songs of power. Huan was able to subdue Sauron when he formed into the greatest wolf ever. And then instead of trying to push the issue he fled rather than start shit up....Sharp wouldn't say shit.....left before deciding to continue trying to fight when Luthien was shown as the next opponent.
So.....mileage aside unless the Lady has some weird loss caveat on her character sheet, which the two given stats both appear to not be, then she should win this.
Maybe Sap Swollen Ungoliant could do some fancy sneaking and streaking here....but not Saul-ron.
The Lady of Pain stomps Sauron. Some of her feats include being a reality warper who changed the rules of the Planescape campaing setting causing the cease of 2nd edition D&D and ushering the start of 3rd edition D&D; she did that in "Die Vecna, Die!". She also has the maze ability which sends someone eternally to an almost inescapable maze located in a pocket universe, since Sauron doesn't have the ability to travel at will between universes he can't escape her maze before the 10 count.
A rare sighting of Farealmer and Transient Guest... lot of old school folks turning up these days.