R1 - Shikai Kenpachi, EMS Madara
R2 - Bankai Kenpachi, Edo Madara (no regen)
If Madara goes perfect sussano than he’s got a shot, otherwise Kenny takes the win.
This. Problem is, Madara IC is very proud and would never pull out PS from the start unless it was someone on Hashirama's level.
Which means, there's a good shot he'll underestimate Kenny, who is easily capable of one-shotting him without PS active.
R2: Kenny easily.
Madara solos most of the Soul Society captains considering that he almost rivals Aizen.
He rivals base Aizen/lower forms of hogyoku Aizen, who would also get sliced up by these versions of Kenpachi. And you can't just apply that logic, given that Madara IC might get one-shotted by Kenny before he even gets the chance to pull out the big guns.
Round 1 - EMS Madara, due to genjutsu. If he summons the nine-tails, it's a stomp.
Round 2 - Bankai Kenny may blitz.
The same Kenny who in the Soul Society arc allowed himself to get caught in Tosen's bankai (which removes pretty much all sensory input), and allowed himself to get stabbed so he could find Tosen, and one-shotted him?
This much-stronger version may very well do the same. Dialing up Kurama feels like cheating, and I doubt the OP wanted Kurama to be in this fight. Kurama does confound things, but Kenpachi has the raw power to compete with almost anyone in the Narutoverse.
Agreed with R2.
Juubidara is about the only competition for Kenny.
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