Hmmm. Yeah, the whole flying thing would probably push it in his favor.

McGyver vs. A Team for escaping the clutches of Dr. Doom.

Actually I think the fight would go to Greymon. Charizard may have the aerial advantage, but Greymon has him beat in size, strenght and endurance. His Nova blast may not hurt charizard as much but with the attacks size it should stun him long enough for greymon to grab him.

Charizard would have to wear him down to win with a whole bunch of physical attacks, Greymon only has to get lucky once.

McGyver, provided he had a paperclip and a shoe lace.

Lelouche vs Naruto in the quest to become a pop idol (henge not allowed).

Since you didn't outlaw Geass, Lelouch in a landslide. "I order you to know that Lelouch is your favourite idol ever!" or somesuch. Or if they're both aware of the challenge, "I order you to hate Uzumaki Naruto!"

Kisame (Naruto) vs. One Lovecraftian Fishperson (The Shadow over Innsmouth), swimsuit cometition. No killing or threatening the judges in any way.

Kisame he just has more style.

Revy(Black Lagoon) vs. Casca (Berserk) All out fight.(no guns or sword just fists)

Going to give it to Casca she just has more experience at hand to hand from what I remember.

If I may issue a new challenge:

Haruhi Suzumiya vs. Inoue Orihime - Recruited as Sailor Sun to single-handedly rescue Sailor Senshi from the elaborate torture chamber of the enemy and help then to recover from physical and mental wounds.

Orihime, Haruhi would 'CHARGE!' get them killed and destroy the universe when she got pissed off she lost.

Watanuki (xxxholic) vs Tohru (fruits basket), cleaning a giant house, who'd do it faster and shinier?

I've got to give it to Watanuki, but only just. Tohru doesn't let her loss get her down, though, and they become friends after.

Akane (Ranma 1/2) versus Sakura (Naruto), Iron Chef battle. Special ingredient is cauliflower.

Uhh... Sakura? Akane is many things a competent cook? She isn't. Sakura needs to be halfway not horrible to win this one.

Sakura (Naruto) vs. Lina (Slayers) flight distance of male annoyance.

Lina, Sakura never got much ground clearance. Naru Narugesawa (Love Hina) may give her a fight though.

Pride (the shadow one from FMA manga/Brotherhood) vs The Smoke Monster from lost, bigger kill count if released in a city.

Lina has magic to keep the male going but Sakura has raw power...still going to give it to Lina.

Pride because Smoke can be countered with enough wind.

Since no question has been asked an old one:

Link (Zelda) vs Gordan Freeman (Half-life)

Wanted to give this one to Gordon at first, however, we have to assume that guns wouldn't work quite as well against Link as they work against combines. After all, Link has magical protection.

Crowbar is fully effective however.

So it comes down to a fight sword vs. crowbar.

Gotta give it to Link, he's just better with that sword.

New one:

Anko(Naruto) vs. Revy(Black Lagoon) scarring men into submission.

Was that scaring them as in "Boo!" or scarring them as in "I'mma cut you up"? If it's the latter, then I've got to give it to Anko. She's the knife nut after all.

And now for something completely different: Ronald MacDonald versus the Burger King, knife fight.

Ronald winds due to the Burger King not being able to comprehend the true form of Ronald's Attack! The true winners though, are all the other fast food companies, who quickly move in to take the loser's place.

Signum (Nanoha) vs SAber (Fate/Stay Night) in a pure battle of Swords.

To anyone who's read Dr. McNinja, you know that Ronald McDonald is a Corrupt Corporate Executive who has experience fighting, while the King is just creepy. RM wins.

MrRigger

Pure swordplay? Saber wins by virtue of the fact that she has a lifetime of experience with non-magical swords, while Signum always relied on magical support techniques. Still, it would be a fight to behold.

Battler (Umineko) vs. Hinamizawa curse (Higurashi) – Can Battler break the loop without Blue/Red/Golden Truths and Witches interference? 5 iterations limit.

Sanji (One Piece) vs. Jiraiya (Naruto) in a duel over a woman. Sorry, I would answer a previous question, but I'm not familiar with the franchises involved.

...Uhhh neither wins?

No matter what they do... the woman still wouldn't go out with either.

Guts (berserk) vs. Belkar (OOTS) bigger badass

No winners they end up killing everything and each other at the same time.

Mion (Higurashi) vs. Light Yagami (Death Note) - Card Games. 1 round of Poker. 1 round of Old Maid. 1 round of Magic the Gathering draft. Games hosted in Mion's club. Both play to win.

Shmion. They cheat, so not even Light would be able to keep up. But due to pride, Light Kills Mion with his Death Note, and an enraged Shion, hopped up on Higurashi-hijinx, snaps and tortures Light to death. Cycle Reset!

Also, I'd have to give it to Hinamizawa over Battler; Regardless of which Battler, his refuseal to believe in the supernatural means he won't succeed in his endevour.

May have been asked before, but, Sasuke (Naruto) vs. Aizen (Bleach), who can win in a complete HAX fight?

Hmmmm. Well, Aizen basically has the ultimate ninjutsu, and we have yet to see how it can be countered. Bleach and Naruto characters are fairly equal on terms of raw speed and power, I would say...but I think I might give this one to Aizen. Then again, Sharingan could probably see this Aizen's bankai, so that would take away his main advantage. And we don't know how strong he is in a raw fight, since he's been so successful at manipulating the situation that he's never had to fight all out. Tough one, but I think I'll say Aizen.

Palpatine vs The Six Flags Guy. Which can do the others' job more efficiently (as a sith lord emperor and amusement park mascot, respectively).

Six Flags Guy. Behind that cheery facade lurks a calculating mind composed of pure malice and evil.

Naruto vs. Luffy, eating contest.