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Jiriaya actually lost on both occasionsDatabook says Jiraiya = Orochimaru.
1.) Past Jiraiya stalemated Past Bloodlusted Oro.
2.) Nerfed Orochimaru = Nerfed Jiraiya
Oro really only goes over Jiraiya if he has prep.
He lost to Orochimaru when Orochimaru left the village similar to how Naruto lost to Sasuke
And nerfed Orochimaru actually beat nerfed Jiraiya, knocked him out for a while, and went to target Tsunade instead