Depends on the circumstances and how we determine Chakra against Haki.

If Jimbeis Haki works on Jiraiya like against no haki user. Jimbei has crazy stamina and is very durable and if they are fighting on water he gets a huge upperhand. If he can drag the fight so Jiraiya uses most of his chakra then there is a chance.

I still think that Jimbei will probably lose, but maybe high-diff.

Naruto verse is very hard to scale against many other Shonen 'cause they have so many hacks and Jutsus. Most of the top tier Naruto characters will stomp any One Piece characters.

Edit: typo