I recapped a few episodes after seeing this thread and they all made me think he could beat jiraiya, OR maybe orochi with luck 1v1, but not tsunade because of Creation Rebirth although it wasnt specific with how long it lasts. even so i recapped the orochi vs 4 tailed naruto and unless you think sasuke can defeat naruto in that state then maybe, because orochi was kinda going toe to toe with him at the time like pain did vs 6 tails, sooo idk if you can take him that lightly. Jiraiya solo'd two or three parts of pain in a 6v1 sorta like how sasuke tried to fight all the kages, cept sasuke had to have his life saved by "madara" (yet again because lets face it...someones always having to save him....) soooo all in all i believe he stands the best shot of winning vs jiraiya, but orochi and tsunade have skills that make them kinda unkillable for abit...orchi shed skin and regenerating (when 4t naru cut him clean in half and he didnt die....) and tsunade has Creation Rebirth, but jiraiya has no techniques like that so thats why i say he has the best shot vs him...