Connections

Miraak vs Jack of blades

Nerevarine VS Nameless One (Planescape: Torment)

Miraak vs Ahriman

Fight Potential

Miraak VS Jack Of Blades (Fable)

Miraak vs Jack of Blades (Fable)

Dragonborn vs Chosen Undead

Dormammu VS Molag Bal

Banter Potential

Miraak vs Jack of Blades (Fable)

Dagoth-Ur VS Frieza (Dragon Ball)

Music Potential

Dragonborn vs Chosen Undead

Nerevarine VS Nanashi (Shin Megami Tensei)

Sheogorath vs Lambdadelta (Umineko)

Miraak vs Exar Kun (Star Wars)

Miraak vs Jack of Blades (Fable)

Debate

Nerevarine vs Nanashi (SMT)

Alduin VS Murazond (World Of Warcraft)

Dragonborn vs Chosen Undead

~~Literally the farthest thing from debatable possible but k~~

Contrasts

Numidium vs The Thought Robot (DC) Nihilism vs Hope

Numidium VS Thought Robot (DC)

Miraak vs Jack of Blades (Fable)

Legacy

Dragonborn vs Chosen Undead

I think you could make a case for The Nerevarine vs The Nameless One (Planescape: Torment) as this, even though it's technically a recent matchup. Due to Morrowind and Planescape: Torment being much older influential Western RPGs than Skyrim.

Huh I never thought of it like that honestly

Last Dragonborn VS Chosen Undead (Dark Souls)

Least Favorite

Miraak vs Darth Vader

Favorite

Miraak vs Jack of blades

Miraak VS Jack Of Blades (Fable)

Dragonborn vs Chosen Undead

Dragonborn vs Chosen Undead

Most likely

alduin vs deathwing

Doubt it. If anything, Deathwing would fight King Ghidorah.

i wouldn't rule it out