Ryougi Shiki vs Emiya Kiritsugu and Kirei Kotomine
Shiki from Kara no Kyoukai, Kiritsugu and Kirei from Fate series.
Mindset: Serious; in character
Knowledge: Everyone knows about each other's powers
Base Shiki with Kanesada Kuji.
Kiritisugu starts with 56 Origin Bullets, he doesn't have an Avalon (it's useless anyways).
Kirei starts with 20 Black Keys and unlimited number of Command Spells.
Win by death/KO.
Team 2 wins due to intel. Take that away and Shiki without much trouble.
Yeah, I thought she would stomp without intel. Kirei would try to fight with his Chinese martial arts, but he would be dead really fast.
Shikis skillset is something that leaves no room for error, if the team just has a general idea about it and nothing specific this is pretty close, actually.