In my opinion Fedor in his prime could beat the Cain of today. Today I think Cain is probably be the more powerful fighter and he doesn't have bad technique either. I'd still put my money on Fedor though since... gut feeling. Whenever I thought Fedor would be at a disadvantage in a certain area he would just go in there and beat them at their own game (minus Werdum). Still I think it's very possible that Cain beats Fedor, just not as likely as Fedor beating Cain.
VIPFFL signup deadline: December 1st