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Sorry slug princess, but I don't see Jiraiya defeating Tsunade in any way possible.
Jiraiya
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Jiraiya was one of the legendary Sannin of Konohagakure.
He was a powerful shinobi, known as the Toad Sage ,
because of his signature toad summonings and his status as a sage.
In terms of speed, ninjutsu and summonings Jiraiya has a huge advantage. Tsunade is way too dependent on melee combat while Jiraiya is far more versatile. He has several ways to corner Tsunade and force her to use the Byakugou, which would inevitably cause her dawnfall.
Jiraiya can control two elements, the Doton and the Katon. This means he can spawn Katon combos from range, or he can use the Swamp of the Underworld to catch Tsunade, he can summon his boss toads to keep Katsuyu busy. Sure, they can't kill her, but Katsuyu can't kill them either. Her acid attack is destructive, but way to linear and easy to dodge.
Swamp of the Underworld
By changing the surface of an object beneath an enemy into mud and creating a swamp, Jiraiya can sink his enemy into the mud. The adhesive, chakra-infused mud ensnares the enemy's body, making it almost impossible to recover one's strength and escape from the swamp. Even in a drugged state, Jiraiya was able to trap two of Orochimaru'sYou must be registered for see links. Jiraiya can use this technique to force Tsunade to summon Katsuyu. This attack is too large to be dodged, so Tsunade's only chance would be to summon Katsuyu. The slug is bigger than Oro's snakes, but a healthy Jiraiya can make a bigger swamp. So Katsuyu is out of the game. I know Tsunade could just send her away and summon again, but the summoning jutsu consumes too much chakra. Against an opponent like Jiraiya, Tsunade needs a lot of chakra, otherwise she won't be able to heal herself.
Katon and other mid-long ranged attacks
Jiraiya is one of the best Katon users in the manga. HisYou must be registered for see linkswas surpassed only by Madara and Obito. This is aYou must be registered for see links, so Tsunade would have a hard time to avoid it. She isn't a speed beast, even Manda barely escaped from it's range byYou must be registered for see links
But ofc this isn't his only Katon. He can use theYou must be registered for see links, theYou must be registered for see linksand theYou must be registered for see linksto keep Tsunade away and force her to use the Byakugou or Sozo Saizei. Tsunade has amazing stamina feats, however she can't regenerate herself forever.
An another way for Jiraiya to force Tsunade using the regeneration is his Nidle Jiso. His hair won't kill Tsunade, but it can cause serius injures and restrain her movement.
Rasengan + shadow clones and shadow manipulation combination
Jiraiya has shown to have a massive chakra supply, enough that he could learn Sage Mode. This means he can use multiple shadow clones to distract and trick Tsunade. He can create an opening by sacrificing one of his shadow clones and use a surprise attacke. AsYou must be registered for see linksshows, Tsunade's attacks are usually linear. When Tsunade destroys the clone, Jiraiya can attack from herYou must be registered for see linkswith a rasengan. Tsunade would tank a rasengan if it hits her back/ chest, but even her regeneration ability has its limits. If her brain is destroyed, most likely she dies.
I won't take the Sage Mode into consideration unless you can prove me that Tsunade can defeat base Jiraiya. I know I used to say Tsunade beats base Jiraiya, but now I'm unsure. Jiraiya outclasses her in almost every way.
This is why I believe Jiraiya defeats her.