Kisame>Oro , even if you are immortal you will die when you run out of chakra. Snake summons useless when you're barried under a mini ocean with someone who can summon sharks.
Kisame+Human Path> Oro +edos ,Human path removes the souls of the edos.
Hashirama< Deva+Asura +Preta , preta absorbs all ninjutsu for defence, deva uses chibaku tensei or concentrated cho shinra tensei to finish him off, deva can also blow the forests away if hashi decides to surround them with trees and pop out surprise attacks from merging with the trees. Asura is just there as back up with his raw power and destructiveness with missiles and laser cannons, won't give hashi time to think up a plan. Plus incredible teamwork because of shared vision. He will lose here badly.
Tobirama < Itachi, all water tech are rendered useless by yata mirror. Edo's sealed away with sword of totsuka. Itachi probably not as smart but the difference in intelligence is almost non existent, although tobirama was said to be a master in warfare and battle strategy. Still what can he do against tsukiyomi, how can he bypass yata mirror, what does he do when his edo's are removed by sword of totsuka, amaterusu burning him? What defence does he have against magatama, can he even compete with Itachi's base sharingan genjutsu abilities? Plus Itachi has the crow with shisui's eye, how much you wana bet he turns Tobirama's edos against him with koto amatsu kami?
Minato=Tobi , I would have given it to Minato since he already beat him and since Minato is like the smartest guy on the series, but I made it a draw because Minato doesn't know about Izanagi, it is the reason tobi beat Konan because she thought she had killed him and then he just surprised her by turning out to be alive, that surprise factor of Izanagi make it a draw to me, Minato might kill tobi and end up getting killed or critically damaged when he let's his gaurd down thinking he had killed Tobi.
Tsunade < Hidan + Animal Path, summoning BOSS LEVEL SUMMON takes up A LOT of chakra, llok at naruto the first time he learned to summon, he had already displayed the ability to summon thousands of shadow clones but couldn't even summon a small toad and needed a mass amount of the Kyubi's chakra to get gamabunta. This speaks volumes about Animal's chakra levels, he was summoning boss level summon after boss level summon throughout the day when he invaded konoha, and those summons are strong too. Animal summons bird and stays in the skies like deidara does with his clay birds. Than he bombards Tsunade and Katsuya with crustacean, baffalo, rhino, centipede, the multiplying cerberus and other summons while he stays safe in the skies, tsunade and Katsyuya won't last that long here, they will die or run out of chakra.
Plus if hidan gets her blood, she would die, and hidan can catch her off guard when she thinks she has killed him. Her rebirth tech might help her get her own element of surprise though, but I doubt she can heal a stab wound through the heart, all hidan won't remove the spike immediately from his heart, he tends to leave it there for quite a long time while he enjoys the pleasure of the pain, she can't heal while the spike is there and she will die surely.
Jiraiya < deidara , pretty obvious, space time jutsu or lightning element are deidara's weaknesses and Jiraiya has neither. Plus Jiraiya is a close to mid range fighter but deidara is a long range fighter, another weakness he has against deidara. Deidara is quite sly and deceptive too and has quite a high IQ, insanity aside. Jiraiya has toad summons but who needs summons when you can animate your explosive clay into whatever size or shape you want. C2 dragon from long range launching explosives, small spider clay C1 attacking from the ground level, explosive mine field will make it impossible for jman and his summons to move about since they don't have lightning to deactivate the mine field like sasuke did,, the jutsu that was dropped on the sand village, strong enough to detonate the whole village if gaara didn't use sand, C4 cellular level disintegration, Jiraiya has no chance against deidara, sasuke was lucky had a sharingan to see the microscopic explosions and lucky he had lightning element, and a bit of plot no jutsu on his side, Jman has neither here, he loses badly because of mismatch. If the situation gets desperate there is always C0 for back up.
Hiruzen< Kakuzu + Naraka path , Hiruzen's Fire and Earth element against all FIVE elements from kakuzu, Hiruzen won't even hurt Kakuzu because of iron skin tech, which is said to be harder than diamond in the data book, its only weakness is lightning tech which Hiruzen doesn't have. Even if by some miracle hiruzen won, there is no way he can win FIVE times on his own, his jutsu arsenal, apart from Minato's reaper seal is pathetic anyway, and don't give us that old age card, chiyo and onoki are older than him and they have showed incredible jutsu and fighting feats and reflexes from chiyo, Hiruzen old age card is just a testament to his weakness. Besides old age does only limits your stamina, speed, and reflexes, you don't suddenly forget your jutsu arsenal and this guy's jutsu arsenal was pathetic, Kakuzu would have a field day. If it came down to it, Naraka can just summon the GEDO MAZO and end the battle with the super fast soul devouring spirit dragon that ate up the souls of hanzo and danzo's army, or just use the raw indestructable power of the gedo mazo, Hiruzen has no chance, prime or not, he hasn't ever even defeated anyone strong, and don't pull the he beat oro card, he LOST to oro, He freakin DIED and Oro LIVED, was still able to fight tsunade and Jiraiya even without his arms, that's very much alive, besides oro was toying with him the whole time only got serious at the end when he almost got sealed, that's the only reason Hiruzen lasted as long as he did. Hiruzen outmatched here, bye bye.
Akatsuki have back up in the form of sasori. Which means hiruko, 200 puppets, iron sand and magnetic field manipulation, and real saori puppet, he can just join any losing side, have 200 puppets join a losing side and turn things around, have kazekage's iron sand crush an unsuspecting opponent, poison senbon barrage, a nick is enough to turn a battle around, Akatsuki win hands down, no competition here.