In the really real world I dont think that Randy has a realistic chance. If Randy was 10 years younger it would be a great battle. Randy has some things going for him, I dont think that Cro Cop could kick as freely as he would want to because it would leave him open to take downs, I think that Cro Cops TD defence is well above average, I do not think that it is the best in the game, or he would have been able to beat Fedor. Pride just does not have that great of wrestlers to test Mirko's take down defence, also once Mirko is down he has difficulty standing back up.
However I just think that Cro Cop has more power, and Randy is just to old to make it a real great fight. Randy is much better at 205 than at HWT, but everybody knows he does not have chance against Chuck so he is fighting in HWT because he has a chance of beating Tim.