i think they are almost evenly matched for the majority of their abilities. what i mean by that is they each have powerful techs and can move up the scale as the battle intensifies
base taijutsu: oro wins. he can transform his body into that of a snake's including extended appendages and limbs, meaning he can fight from a distance
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. keeping his distance is useless for jiraiya. he kept up with 4 tailed kyuubi and pretty much bested jiraiya in their encounter in part 1, breaking jiraiya's rib. the only time i can think of that occuring was when they clashed, oro's bite vs jiraiyas underworld spines. furthermore, oro can fuse with inanimate objects similar to tobi
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jiraiya's underworld spines is still overcome by simple use of the kusanagi blade, which id count as taijutsu.
base ninjutsu: jiraiya probably wins. toad mouth binding, swamp of the underworld, raging lions mane, and toad oil bullet is fairly potent. if oro is in the toad mouth, he might be able to cut his way out with kusanagi however. or turn into his true form but more on that later.
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here jiraiya can defeat oro's big summons but oro himself will either phase into it with attack prevention or use
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. and if jiraiya tries to summon, oro can restrict and bite him with many hidden shadow snake hands, which are stated to be poisonous snakes powerful enough to capture opponents.
summons: oro wins by a landslide. summoning ma and pa takes time, time oro wont give him as he no doubt has seen SM before.
furthermore imo manda is way stronger and more dangerous than gamabunta. he felt confident in his ability to kill orochimaru after realising he cant use jutsu, and the only reason he hasnt betrayed oro is because he thinks oro is stronger. hes able to avoid any attack by shedding his skin as a decoy, and then travelling underground. the power of his size and strength was enough to almost overpower both gamabunta and katsuyu at once, dodge katsuyus acid and gama's oil, but tsunade put a stop to him by attacking from above with her strength. and his durability was enough to keep him alive for a while after being hit by deidaras explosion.
furthermore, he has
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where hundreds of snakes all with kusanagi daggers descend upon the opponent in a huge wall of snakes. Kn4 defeated it with a chakra shockwave. but jiraiya has little that could manage it without SM.
and finally he has sanjuu: triple rashomon, which is a tower of 3 large defensive gates. in the time it took bijuudama to leave Kn4s mouth, oro thought to himself, put his hands on the ground, summoned the gates, and take the blast. this perfect for taking on other long range attacks from jiraiya, namely gama and jiraiya's toad flame oil bullet if manda cant do it, or gama's water jutsus.
advanced ninjutsu: now that we covered that, lets move on to SM vs oro assuming jiraiya enters it.
if jiraiya uses senpou: hair senbon, oro can defeat it by using wind release great breakthrough or by his fire jutsu he used on naruto.
the summons wont be leaving oros side any time soon so he can summon and reverse summon rashomon however he wishes. if need be, oro can close in and place a Cursed seal on jiraiya's neck. this will not only paralyse him but he has only a 1 in 10 chance of surviving and gaining more power from it. but it wont matter if he does because he will be so in pain that he wont be able to move and kusanagi will pierce his skull. against pain, the first thing jiraiya did was the goemon jutsu. this can be defeated by oro's gates, or by attack prevention technique avoiding it and enabling him to use clones and manda to attack from behind.
with formation of ten thousand snakes active, ma and pa may not get a chance to do much of anything.
in taijutsu, jiraiya would stomp. so oro's only hope here is keeping a relative distance and bombarding him with extended kusanagi, wind release and snake summons. if attacks do land, oro can heal himself via body shedding or gathering of the snakes. in the fight with naruto, losing an arm barely even phased oro but against pain, jiraiya losing an arm effectively ended the battle.
trump cards:
jiraiya has two. i know surprise surprise. its barrier toad gourd prison, and demonic illusion: toad confrontation chant. oro isnt stupid enough to fight SM users in taijutsu so the barrier might trap a snake or two. toad chant takes a while to set up and oro wont give him the chance, because he will have transformed into the mighty dragon god
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. hiding in this thing's mouth, hes safe from nearly anything jiraiya can throw at him. it took the sword of totsuka to slice off its massive heads which in turn didnt even slow it down.
if thats not enough, orochimaru will use
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and bring to the battlefield hashirama senju and tobirama senju, or any number of kabutos summons since they no doubt got madara's DNA together, and sasori's. its clearly stated by kabuto, that oro perfected it.
that brings to the table the versatile wood element techniques including defensive wood domes, large trees and roots for capturing, flower tree world for putting people to sleep and the darkness genjutsu which will force jiraiya to rely on senjutsu sensing.
as well as tobirama's powerful suitons which are a perfect counter to toad flame bullet and deep fryer, and tobirama's sensing abilities where he can sense the numbers and exact location of opponents. he also supposedly has teleportation near the level of minato namikaze.
if thats STILL not enough, oro can go back into his true form, use of his kusanaig snakes to cut him open which releases a paralysing poison vapour. it affected even sasuke who had surely been made immune to most poisons by orochimaru.
intelligence: orochimaru is one of THE smartest characters in naruto history. he had his paws in EVERYTHING. root, akatasuki, konoha, research into senju hashirama and rikudo sennin etc. his ultimate goal was reaching the rinnegan and learning all techniques in the world. jiraiya by comparison is like naruto to oro's shikamaru. jiraiya is really alot like naruto whereas oro is hailed as a once in a generation genius bursting with talent even more so than hiruzen sarutobi, who was said to have been called the professor. which is incredible. his vast knowledge carried over to combat and we saw him fight amazingly against anko, instantly outmaenuvering his own student, and in the battle with KN4, he kept pulling out new tricks while simply smiling at any damage done to him. and his plan for taking sasukes body would have worked if sasukes will didnt overpower him. which he couldnt have predicted.
the only point in this battle where oro is in danger is in the beginning exchanges since jiraiya has slightly better ninjutsu. orochimaru is without a doubt the superior sannin.
