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Kirei fights his old Servant (Hundred Faced Hassan vs Kirei Kotomine)

I mean you never specified ovo

Angra Mainyu GG but even without it, Kirei has full info on what Assassin can do while Assassin has seen almost nothing of what Kirei is capable of. The bodies also aren't all combat oriented with a large portion being meant for other tasks and their stats split between all 88. Kirei should outskill the majority of them and can amp with Command Seals to fight the stronger ones along with sacrements that are super effective against spiritual beings, 100+ Black Keys and his pseudo precog.

Without AM, I see Kirei fending them off while retreating since he obviously can't physically fight them all as even other Servants can't face them en masse. If they had to chase him down and fight cqc, I'd say he could pull off a slight win but since running into them is suicide and they can just wear him down with range spam, Angry Manjew is his saving grace via blocking everything they have and being nigh perfect for fighting spiritual beings.
 
Kirei could not survive in CQC against Hundred Face. If he faces them head-on he gets mobbed, while if he runs away or stands still for too long he opens himself up to being surrounded by the vastly faster assassins.

Besides, Presence Concealment. Kirei can't detect Assassin and gets his throat slit by a dirk in the dark. Knowing it exists won't help, and Kirei's pseudo-precog doesn't help either since it works by following fine-body motions.

His only chance is by flooding the area around him in Grail Mud, and even then, Hundred Face can just take the high ground and chuck dirks.

Voting for Hundred Face.
 
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