Itachi vs. Naruto : Itachi for obvious reasons. Probably one of the most powerful characters thus far in the manga. Sacrificed himself to "save" his little brother. Tsukiyomi, Amaterasu, Susanoo with sword and shield. Too much for Naruto to handle. GG.
Pain vs. Naruto : In a battle where both characters are trying to kill each other, Pain wins here. 6 Paths are too much, without Hinata's interference Naruto would be a shed skin of the 9-tails right now.
Kisame vs. Naruto : Interesting match up. The only problem is we don't know the extent of Kisame's abilities. His sword eats chakra and prevented Naruto from entering fox mode earlier in the series. Would the sword be able to handle Sage chakra? Its not a person, so maybe it wouldn't turn into a frog statue. IMO the sword would be able to handle the sage chakra, thus Naruto wouldn't be able to use either Sage, or Fox mode. Without those two Naruto is in big trouble. Kisame wins.
Sasori vs. Naruto : Another interesting fight. While hes getting better, Naruto has been shown to be a little too aggressive. He may end up rushing in head first and get cut, thus being poisoned and dying. He he actually takes the time to realize "oh, the puppets have poison coated weapons" I think he wins this easy. One expanding Rasenshuriken is going to take out a shitload of puppets. Winner: Naruto.
Orochimaru vs. Naruto : Orochimaru has this one in the bag. Too many forbidden jutsu and too strong of a will to survive. He has his special extending sword, as well as snake mode. He can turn into that humongous hydra, and take the fight.
Naruto vs. Deidara : Naruto wins this one. The only problem is him avoiding C4 Garuda and the suicide bomb. I think in sage mode he would be able to sense the micro bombs and get out of the attack radius, and then maybe he could avoid the suicide bomb by using Pa or someone to reverse summon to the toad mountain.
Naruto vs. Kakuzu : Obviously Naruto, already happened.
Naruto vs. Konan : Don't underestimate Konan here. She did train under Jiraiya and seems to have some sort of paper related KG. I think she puts up a good fight, but in the end loses.
Naruto vs. Hidan : Naruto LOLS Hidan to death.
Naruto vs. Madara : We don't know if Madara can even attack, but considering he told Sasuke he would kill him if Sasuke betrayed Akatsuki, I'm guessing he can. Madara seems to be playing with everyone at this point, so hes going to take this one. Eventually they will fight when Naruto is stronger, and Naruto will win.
Naruto vs. Zetsu : No idea really. Zetsu took out the Mizukage with literally no effort. He seems to be strong, but when its a 1v1 fight and both opponents are focused on each other I don't think that jutsu would work. Naruto wins this one.
