First off, comparing Kimbo and Tyson is a hilarious false-equivalency. As an amateur, Tyson won two Junior Olympics boxing gold medals (winning every fight via KO). Tyson was more than just a brawler, at least for the majority of his career. That is part of why it was so sad to see him fall from grace so hard... But, I digress. Tyson was a technically gifted fighter, and though not a well-rounded pugilist, his technique was dominating.
Kimbo got famous by beating up wannabe tough guys in back yards, and got handled by pretty much everybody not named Houston Alexander. He got jobbed to Seth Petruzelli, the last time he and Shammy were supposed to fight (Shamrock couldn't get medically cleared because of a cut he sustained over the eye, during training).
If Shamrock is smart, he will make Kimbo chase him, and annoy him with some light jabs and focus on footwork. Make Kimbo over extend, over commit, to a combination, shoot, and then it's over. If I was coaching Shamrock, I would suggest shooting, clearing the hips to take sidemount; go for a Kimura or Americana, and as soon as Slice turns his hips to relieve the pressure/escape, isolate one of his legs, and go to an achilles lock with a heel hook being the consolation prize, if Kimbo tries to turn out of the achilles lock.
But, that's just my opinion.