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Post two villains who could fight each other, the next one who replies decides who could win and posts new fighting round etc. I start.

Chernabog (Fantasy) VS Devimon (Digimon)

Chernabog because Devimon doesn't seem like the official evil unlike Chernabog appears to be.

Ghen (Riven: The Sequel to Myst) vs. Saavedro (Myst III: Exile)

Troll King vs. MrHcFortan

Troll King has more youthful vitality.

Jareth The Goblin King(Labyrinth) vs. NightmareMoon(MLP:FIM).

Jareth because he's not a pony though he is gay.
Nihilanth (Half Life) vs. Companion Cube (Portal)

Nihilanth, because of Xen syndrome.

Colonel Kurtz (Apocalypse Now) vs. Rudolf Von Sturmgeist (Medal of Honor: Frontline)

Colonel Kurtz because Movies.com ranked him as the best evil transformation at one time.

Ghen (Riven: The Sequel to Myst) vs. Saavedro (Myst III: Exile)

Saavedro. I was never particularly impressed with Ghen's craftiness.

Johnny Lawrence (Karate Kid) vs. Chozen (Karate Kid, Part 2)

I haven't seen karate kid. So i'd assume the first one.
Troll face Vs. Inglip

Hmm, Troll Face is immune to all non-physical attacks, but Inglip is a lord of darkness….
Troll Face wins the cool contest, but ultimately would be crushed by Inglip.

Farquaad (Shrek) vs. Yzma (Emperor's New Groove)

Yzma, cause that bitch can actually do something herself.

Coolcat vs. Cooldog.

The cat has text. It wins.

Cirno (Touhou) vs. Utsuho (Touhou)

OH SHI- BATTLE OF THE DAKKA! 6BALL VS 9BALL. ICE VS NUCLEAR FUSION! FAIRY VS HELL RAVEN! WHO WINS!?

So you admit you're a villian.

Never seen Touhou…I'll say Cirno then.
Cooler name, and too lazy to look them up.

4kids vs. Ms. Finster (Recess)