Lol odd time for this to be bumped but I wanted to give my thoughts anyway.
Round 1:
Jiraiya vs Obito - Obito was physically even with Kakashi including in speed so blitzing is an option. Even ignoring that there's no real way for Jiraiya to touch Obito unless he uses Frog Song, which takes too long.
Itachi vs Danzo - Danzo's only ever resisted Genjutsu from Sasuke which we made clear was weaker than Itachi's, so it doesn't seem like he can resist Genjutsu.
Pain vs Sasuke - Without prior knowledge Sasuke has no way of contending with Pain. He wouldn't know to take out Human Path so all the pains could just heal from all his attacks and Preta Path could absorb them all. Sasuke doesn't have the feats to tank Shinra Tensei and he'd get dragged out of Susanoo. Aside from that Sasuke is just too outclassed in raw power.
Naruto vs 5 Kage - KCM Naruto is the perfect counter for the Kages. He has shadow clones that make numbers less of an issue and they can fight on par with Kages as proven against the Third Raikage. Naruto has ways of beating them all alone. He's faster than the Raikage as proven when they fought, outclasses him in strength and actually has versatility. Onoki, Tsunade and Mizukage get blitzed. Onoki might not but he doesn't have the feats to react to a Rasenshuriken. Rasenshurikens would also take down Gaara.
Minato vs Kaubto - Minato also has Sage Mode and should have the advantage up close given he's more skilled and has teleportation.
Killer Bee vs Deidara - Deidara barely reacted to Sasuke and was amazed by his speed so IMO anyone faster than Sasuke can blitz Deidara, which Bee is by a significant margin. Even ignoring that Deidara has no answer for Bijuu bombs.
Kisame vs Orochimaru - Oro has no way of combating him within the water dome and he'd get drained.
Might Guy and Kakshi vs Kakuzu and Sasori - lol do I need to explain this?
Round 2:
Itachi vs Obtio - Obito has never shown the ability to resist that level of Genjutsu, and Itachi's faster.
Pain vs Naruto - Without starting in Sage Mode, there's no reason Pain couldn't just do what he did before - pull him over and have Preta Path drain him. KCM isn't stronger than Sage Mode by feats so Preta could restrain him just fine and without the negative effects of absorption this wouldn't backfire.
Minato vs Killer Bee - He's already proven faster and more skilled and with teleportation he should be able to get Bee in an unfortunate position like he did before.
Kakashi and Might Guy vs Kisame - Guy already beat him and there's no reason he wouldn't again.
Round 3:
Pain vs Itachi - Rinnegan sees through Genjutsu and Itachi would waste a lot of energy trying. Actually Itachi would waste a lot of energy in general misusing his attacks on Pain without prior knowledge while one good Shinra Tensei would end Itachi.
Minato vs Kakashi and Might Guy - Guy doesn't have speed feats to avoid getting blitzed without gates and Karachi isn't fast enough to stop him. Minato is significantly faster than Kakashi and can teleport around all of his attacks and Sage Mode makes it worse if he uses that.
Final:
Pain vs Minato - Shared vision will counter teleportation tactics and he lacks the means to hurt Asura Pain or the summons unless he opens with Sage Mode which he wouldn't, and Deva Path vastly outstrips him in power and can one-shot.
So Pain wins.
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