Honestly, Jiraiya would win this. I'm unsure whether any of his attacks can pierce the Susano'o, but I'm pretty sure he has something that can waste the shield. Even if he doesn't, Jiraiya would easily outlast Sasuke. The Susano'o, Sasuke's only truly reliable defense against Jiraiya's vast array of lethal techiques, not only drains chakra like a bitch, it leaves the user in agony. Sage Mode actually reduces the amount of (human) chakra used per technique, compared with the result.
Jiraiya has been around long enough to know how to avoid Tsuskuyomi,which Sasuke is vastly inferior with compared to Itachi, and both Amaterasu and the chakra arrows require some chakra-buildup before use, enabling Jiraiya to dodge them.
If Sasuke tries to take on the pervert in taijutsu, he just loses. You can't block what you can't see, and the Kawazu Kumite is invisible to the Sharingan, which Sasuke relies heavily on.
The "Frog Song" genjutsu is interesting. In my view, it would go through the Tsukuyomi, leaving Sasuke paralysed until the constant chakra drain finished him off. The Frog Song is auditory, and as Sasuke can hear things through the Susano'o, he's vulnerable.
Are there any counterarguments to my POV?