Round 2:Sand Siblings wins med diff (facing Sand Siblings is Like facing Six Paths Of Pain)
Lol
Anyways, what is up with the underestimation of Ero Sennin here? Loses each one except 1?? Oh please...
Round 1: Jiraiya wins with low difficulty. Mist is blown away by Ma's fuuton, and they all get burned to death by Senpō: Goemon or a giant, sage mode and oil enhanced katon, which has a larger AoE than Mei's water pillar.
Round 2: Jiraiya wins med diff max.
- Trollkage-sama was countering Gaara's sand shields and restraints simply by secreting oil from his body, Bunta can spit out large quantities and make Gaara's sand null. It's even worse for Gaara if the location isn't a desert. The quantity and quality of his gourd sand is high, but not enough to shield them from Senpō: Goemon, large scale katons, multiple Ōdama and maybe a Chō Ōdama Rasengan, all powered up by senjutsu chakra.
- Temari (sorry Ice) and Kankurō are no match here for Jiraiya's firepower. Kiri Kiri Mae's AoE is much smaller than Gamayu Endan, and her other wind techniques get overwhelmed by smaller katons. Kankurō is even worse, Jiraiya can create shadow clones and mow down his puppets with Kebari Senbon and small fire techniques, or maybe even Ma/Pa's tounges and katon/fuuton combo.
Round 3: Jiraiya wins with high difficulty.
- Darui's black raiton and ranton are still ninjutsu, which means that they can be stalemated or overpowered by medium scale/large scale katons in conjunction with Ma's fuuton to weaken the lightning. Shee's only function here is as a medic and a sensor; genjutsu is a non factor in front of sage sensing and the partner method. Even then, Shee won't have enough time to heal anybody with the onslaught of Jiraiya's sage ninjutsu.
- Ay is trouble here I'll admit, with his v2 speed and strength. However, he still has to charge chakra on his feet to use shunshin like he did to dodge Amaterasu. Ma's fuuton dust cloud makes for a good distraction while Jiraiya makes several shadow clones and has them all use a transformation jutsu to make it look like they have Ma and Pa on their shoulders to fake out Kumo. One of the sage trio can also summon another boss toad or toads to attack the Kumo jōnin and distract Ay while Ma an Pa prep the genjutsu, which I think only took half a chapter to prep (can't be THAT long).
Round 4: Jiraiya med difficulty.
- Torune and Fū suffer the same fate as Temari and Kankurō, genjutsu won't work, bugs get burnt to a crisp, Pa's tongue splits Fū in half, fuuton/katon combo end Torune, etc.
- Baku gets greeted warmly with a nice and simple katon in his mouth. Dissapears several seconds after he gets summoned. Danzō's izanagi spam and his respawn speed could be a problem, but Jiraiya can make shadow clones to cover the his perimiter, and even have them all use a SM enhanced sensing barrier if needed. From there on, nothing Danzō does will go unnoticed, and nothing he has in his arsenal is a match for even base Jiraiya. I assume KA is restricted.
Round 5: Jiraiya med diff
- Kurotsuchi and Akatsuchi are even worse off than the other kage bodyguards
- Ōnoki is not prepping jinton here with the speed and scale of Jiraiya, Ma, and Pa's attacks added with the leaping power of boss summons. Ōnoki will have to make rock golems to protect them from Jiraiya's sage ninjutsu spam, and even then they can be utterly obliterated by Chō Ōdama Rasengan, or overwhelmed with large scale AoE attacks like Senpō: Goemon, and Gamayu Endan.
Bonus round: He probably loses this one. Tsunades's elites are on a whole other level compared to the other kage's bodyguards, and Tsunade herself isn't a slouch either when backed by strong allies.