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HST may win with the combined efforts of the Naruto God tiers, especially if Krillin holds back and doesn't want to kill them like he did with the Frieza soldiers
Yhwach is the biggest problem, outside of that, I don't think that anyone has the speed and firepower (except Kaguya and Ywach) to take him down.
He honestly lose if he holds back, there are people who can match or hax him. If he's bloodlusted or serious though, he could instantly wipe out all but the big players with ease. At that point, idk how he'll deal with the immortal Kaguya (BFR by throwing her into space ?) or even Yhwach, who has roughly equal firepower and a much better hax.
TL;DR : Lose to combined hax and firepower if ic, lose to hax and firepower from Yhwach in round 2 after probably killing or defeating everybody else.
He's faster tho, so he could try to blitz and punch Yhwach but idk if he can do that.
Krillin solos, but barely. The Bleach and Naruto have really good hax, but Krillin has enough speed and power to defeat them, especially when he's going all out.
trio wins ( barley ) Reason krillin has shown he can be some what Arrogant And against humans or people he feels are weaker than him or his friends he has showen to underestimate them and not go all out and that would give the trio the advantage they would need krillin would make quick work of the weaker guys ferther reinforcing his mind set until the they strong guys come he still holds the physical advantage but when he goes to use and attack someone say kaguya or jubi madara and hits the TSB and finds his hand (or foot) is gone and that is when they lanch their true counter attack kaguya being able to instantly teleport gets next to him and attacks and then obitio or madara since they can use TSB use theirs and take off more limbs or do more damage then genryusai with his bankai comes and designates him ( because Dispit the DB -verse great durability they don't do well with extreme temperatures example the fight between the metal man and vegeta and how they are constantly avoiding lava ) that and he has no way of dealing with the immortal people of the trios side even blood lusted i cant see this going much different aside from him bloing up the planet but with minatos space-time barrier he could redirect that attack at him causeing even further damage and if he does destroy the world there is nothing to say kaguya can still be there ( and arguably a few others ) since she can't die and krillin does not have any sealing techniques or someone on the trio side could BFR him or put him under genjutsu ( i say genjutsu because for it to be even they have to be able to see and interact with the bleach characters so everthing woukd have to be equalized and all of there attacks would have an equal chance at working ) or if dont like the genjutsu the trio also has aizen and shinji if that sutes you better that you have tessai and the bleach team who can freeze time giving them an advantage as well and on that note they have barragon who with his ability would work and gins as well ( his bankai cellular destruction anyway) there is also balckbeard with is BFR awell and since this is no hold bard there is no way i cant see tessai just freezing time and the rest attack there powerful and some durability ignoring attacks and there is no way for krillin to know who to attack first to make sure all the hax don't happpen That is just an example but i believe the trio takes this with high difficulty