Well... Naruto wins.
Jiraiya died before Naruto began his sage training. So under these circumstances, he doesn't know that Naruto can go sage mode. Thus, Jiraiya will probably just stick with his base form thinking he can take on Naruto with just that. However, Jiraiya still does have Naruto beat in every regard if it's base-to-base.
Naruto, on the other hand, cannot compete with Jiraiya in his base form. He does however have two aces up his sleeve:
- Naruto has the rasenshuriken during this time. Jiraiya probably has heard of this but he has never seen it as Naruto was not allowed to use the technique again by Tsunade. So Jiraiya will probably crap his pants once he sees this technique.
- Naruto can summon clones to go to mount myoboku to gather sage energy, thus allowing him to enter sage mode much faster than Jiraiya.
If Naruto manages to enter sage mode, Jiraiya is pretty much fricked. Jiraiya cannot enter sage mode as fast as Naruto can and he cannot maintain it as long as Naruto can.
Naruto takes it 8/10
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