SM Jiraiya, Zetsu Orochimaru, Tsunade
SM Jiraiya's the only real heavy hitter here, and with full intel he'd be the priority. I have a severe lack in his and the Sannin's ability to safe guard Jiraiya from an enhanced Raikage or strike from Muu. They'd win with medium difficulties, or so.
The Dead Kages likely win with high difficulties. Bee possessing Samehada makes typical Raikage strategies harder, and with both being durable and speedsters, Mu'd also have a harder time. Though if Ay can be taken out, which he likely would be, I think Bee would be over whelmed.
I really want to say the Akatsuki win this. Depends how quickly Itachi and Kisame act, if Kisame moves to gain field control, I'm inclined to believe they win. Wouldn't put it past the Kages to take Kisame out early on in the battle and leave Itachi alone, though. Could go either way at the end, high difficulties.
Six Paths of Pain (CST restricted)
Probably the Dead guys, high difficulty. Chibaku Tensei is the clincher, but the Third Raikage is likely able to bust that in a minute or so when he inevitably collides with it.
EMS Sasuke (PS restricted)
I'd honestly go with Sasuke. I have my doubts on the third alone surviving too long, or making an impact alone. Sasuke should be capable of keeping up with him, well enough to not always be directly in danger. And if Muu opts to split, Jinton, the biggest threat, is over with. If he doesn't, I'm not sure how Ay doesn't get hit by Enton or Amaterasu. Sure, he'll survive and continue fighting after being struck. But the fire'll continue to grow and likely have a prolonged effect on his chakra shroud. It'd also present a real threat to Muu, if they decide to go with a faster approach to fighting Sasuke. Unless it's a limb (Arm), then the raikage's fine. Muu can cauterize the wound and give him some more time to fight. Still wouldn't be ideal.
The only way I really see them winning is through outlasting Sasuke or if the Uchiha loses track of Muu long enough to be hit by a Jinton. I'd go with Sasuke winning with high difficulties more times than losing.
DSM Kabuto (ET restricted)
Hard to say, not sure what Kabuto could do to really off Ay, other then possibly aiming for his scar if/when he's trapped in a genjutsu/hit by white rage/paralyzed by the white snake venom.
The past generation mid to high diff. Izanagi's the only persisting threat, but I don't see him doing much damage to Ay, who should have good enough reaction time and striking speed to keep him at bay for a while. Muu can always allow half of himself to be absorbed, too. But not sure if Obito would readily fall for it. Anyways, don't see Obito really putting them down.
7 Gate Gai and 1MS Kakashi
I'd have to say this is similar to the Akatsuki match up. I wanna say the Konoha team wins, but if kakashi doesn't use Kamui early on, on Ay, they really don't have the best shot. I doubt Gai can really get through Ay's durable skin, or do so effectively. And a lightened Ay probably can deal some damaging blows to Kakashi, I wouldn't doubt the combo being roughly V2 Ay speed or something similar. Kamui'ing them after that would be hard. Whoever pulls the trigger first, wins.