Board Thread:Versus Debates/@comment-26005711-20150518115443/@comment-26518343-20150624144459

It'd most likely be a draw, as I don't see either of them being killed in battle.

Orochimaru would just retreat or disappear if the tide was turning against him. Self preservation is his thing.

Even if he was at a disadvantage in the fight, Jiraiya would still be resourceful enough to defend himself against Oro's more powerful attacks and jutsu's. He knows him too damn well. It isn't like fighting Pain, in which he jumps into battle with a ninja more powerful than Orochimaru completely "cold" (no knowledge or prep on his opponent).

In the long run, if Orochimaru did not retreat, I'd bet on Jiraiya crippling him much like Hiruzen did at best, but Oro would live. In this scenario, Jiraiya might spend a week or two sharing a hospital room with Kakashi afterwards but he wouldn't die.