Well if you wanna be vague about anime they did create some animeish spider man cartoons.
Ya sorry about that, but I mean spiderman or deadpool in general movie or comic.
I personally side with deadpool though.
Shana from Shakugan no Shana
Saito Hiraga from Zero no Tsukaima
Equipment: What they have on them.
Abilities: All of them that pertain to their equipment and their being.
Knowledge: Nothing, but they are fighting :D.
Who Is Going To Win? o.O
Im personally would go for Saito just because he seems alot more adept with his sword, and he can take alot more damage. (Oh and he took on an army of like 7 million or sumtin like that.)
I would just like to point out how Naruto grabbed a massive 60 ton stone and smashed pain with it like a hammer, also when he explodes pain's planetary devastation or condenses his chakra to shoot a massive blast. Just SAIYAN...Oh and if you watch when Naruto fights he causes absolutely way more destruction. And Luffy's rubberness could be easily ripped right? I mean he does rip face Orochimaru's face off.
Just showing his condensed chakra....skip to 2:10.