Silvers Rayleigh vs Jiraiya

The legendary characters who trained the series protagonist, Rayleigh the "Dark King" and the Pirate King's "Right Hand" vs One of the legendary "Sannin" Jiraiya the "Toad Sage".

.They have knowledge about each other

The fight takes place in the Sabaody Archipelago.

I'd say Rayleigh. Even in his old age he was casually fighting with one of the most powerful characters shown in the series so far.

Yeah Rayleigh would probably win out despite Jiraiya's versatility. Really wished Jiraiya could've lived to receive the benefits of Kishi's power spike.

Well, I mean... He did sorta hold his own against Pain without prior knowledge if his powers, and Pain is still one of the strongest characters even if he's not on the same level as Hashirama or the Otsutsuki's.