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JDS and Cain would both KO him standing.
He cant take either one down so JDS will do what he does best and Cain wont want to mess with the BJJ of Werdum so he will do something similar to Cain-Nog and Cain-BF. crisp shots, in and out, quick end.
Werdum has a really underrated chin though, he has only been KOd once by a massive Cigano uppercut and boy has he faced HUGE hitters. I could see him eventually luring Cain to the ground and things could get interesting, specially if he is in shape.