Jiraiya wins with medium to high difficulty
- Fūka Hōin and Needle Jizō followed by Senpō: Kebari Senbon take care of Amaterasu
- With full intel, Jiraiya anticipates Susano'o arrows and avoids them with his sage mode enhanced mobility and reflexes. Also, Shima and Fukasaku can sense the buildup of Sasuke's MS techniques and counter accordingly/warn Jiraiya in advance.
- Snake summons get crushed by Food Cart Destroyer, trapped in Doton: Yomi Numa or incinerated by Senpō: Goemon
- Hawk summons get taken out or pressured heavily by Kebari Senbon, Katon: Dai Endan/Gamayu Endan, or by toad summons. Sasuke won't simply be able to spam arrows from the sky.
- The Susano'o Sasuke had when he fought Kabuto isn't going to protect him completely from techniques like Goemon or giant, oil-enhanced katons. Jiraiya could even coat the susano'o with Gamayudan or Gamabunta's own oil to increase the effect.
- Although it won't work more than once (perhaps twice), Jiraiya could clone feint Sasuke by oculting his real body inside the shadow of one of his clones using the Toad Flatness Manipulation technique. This strategy could create an opening for a decent blow even if it's rather risky.
- Lastly, Frog Song would end up leaving Sasuke open and susceptible to attacks from Jiraiya and his boss summons.