Score Card:
Spike(Cowboy Bebop-Anime) d. The Punisher(Marvel Comics)
Optimus Prime(DW Comics) d. Iron Man(Marvel Comics)
Inuyasha(Manga) d. Harm(DC Comics)
Darkseid(DC Comics) d. Buu(DBZ-Manga)
Megaman ? Cyborg
Stewie Griffin(Cartoon) d. Vril Dox(Dc Comics)

Main Comics(TT, Outsiders, JLA, etc): 1
Manga: 2
Video Games: 0
Alt. Comics(Based on a show/cartoon):2
OC(RPG characters included if there were any changes): 0

Now that I think about it, I really could have made the Harm vs Inuyasha a four way with these two to make the ultimate dark battle. But either way, this match works really well too. Dark evilness all over the place! And for those non-versed in both Spawn and Jackie Estacado aka The Darkness I'll fill you in.

Spawn Profile

Profile
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Real Name: Al Simmons

Location: Hell

First Appearance: Spawn #1 (1992)

Created By: Todd McFarlane

Publisher: Image Comics

Team Affiliations: None

Currently Seen In : Spawn

Powers:
Physical Regeneration
Flight
Teleportation
Super Strength and Endurance
Shape-Changing
Blasts of Energy
Mental Control of Chains in his Armor
Armored Body

Interesting Fact: Spawn's cloak is actually a living entity.

Origin: Al Simmons was a top assassin for the CIA. When he was betrayed by his own men, he went to hell and made a deal with the demon Maelbolgia to see his wife one last time. Al was sent back to earth with little to no memory of his past, a hideously scarred body and face, and supernatural powers. Being called the Spawn, Al leaned his mission in life, to lead the armies of hell in a war to destroy heaven and make Maelbolgia king of all. Spawn refused and has since had to fight enemies of heaven and hell, all the while trying to protect and get back to the women he loves, his wife Wanda.

Jackie Estacado / The Darkness

This was originally published in 2003 in Top Cow: Book of Revalations. I'm reprinting it here for your enjoyment and so that you can understand Jackie better. I have, however, updated it and expanded upon it, and my additions are in italics.

Bio Data

Real Name: Jackie Estacado
Aliases: none
Current Occupation: former assassin (organized crime don)
Date of Birth: March 25th, 1975
Marital Status: single
Major Enemies: Cousin Paulie, The Angelus, Lord Sonatine
Known Allies: Butcher Joyce
Sometime Allies: Sara Pezzini
Previous Allies: Tom Judge, Jenny Moreno
Base of Operations: New York City, NY

Physical Description

Height: 6'1"
Weight: 195 lbs.
Eyes: Brown
Hair: Black

Powers and Abilities

Intelligence: Above Average
Strength:
In the light - athletic level
In the dark - superhuman level
Speed:
In the light - athletic level
In the dark - superhuman level
Fighting Skills: expert in martial arts and various weapons
Weapons Used: Large caliber handguns
Special Powers: The power of the Darkness grants Jackie the ability to create virtually anything he wants, as long as he has the knowledge of how it works. In the past, Jackie has used this power to create an armor to cover his skin, as well as razor sharp tendrils, and monstrous creatures to do his bidding (known as Darklings). Jackie has also been seen to use The Darkness to create guns, a doppelganger of himself, cocoons to shield his allies, to travel through shadows, to heal himself, and to absorb extraneous fragments of The Darkness.
Limitations: The power of The Darkness can only be used in the dark. Anything Jackie creates with the power will vanish in the light of day. Jackie must also deny himself one of his true loves, the pleasure of women, for the power of the Darkness is transferred from father to son at the moment of conception, killing the father in the process.

Bibliography

First Appearance: Witchblade #10

Biography

Jackie Estacado loved his life. As a hitman for the mob, Jackie was always the final solution to a problem. But for him, the problems were just beginning. On his 21st birthday, Jackie inherited the power of The Darkness. Since then, Jackie's life has been full of a great many other things, from battling the power known as The Angelus to fending off the evil Lord Sonatine. These conflicts only served as a prelude to the most difficult time in Jackie's life, the betrayal of his Uncle Frankie and the death of his beloved childhood friend Jenny. Avenging Jenny's murder, Jackie caused an explosion that not only took Frankie's life, but his own as well. Now, thanks to the incredible power of The Darkness, Jackie has returned from Hell, lost in a world he once knew. In his absence, another member of his mob family, Cousin Paulie, has risen to power, and like Frankie, he has begun to attack those that Jackie cares for. But is Jackie ready for the battle ahead?

lol And after a whopping 3 votes Jackie is the winna!