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I'm picking fighters who fought in the UFC, but the versions of them from the given dates, not the dates they fought in the UFC.
I'd pick:
Murilo Bustamente from 1993
Sakuraba or Big Nog from 2003
Cain from 2013
Francis from 2023
I'd pick:
Murilo Bustamente from 1993
Sakuraba or Big Nog from 2003
Cain from 2013
Francis from 2023