kimbo really isn't that great of a fighter, mma or his so called "street fighting" which were nothing more than bare knuckle boxing fights, (not street fighting). but you could start by contacting American Top Team where he trains, or finding out who his manager is and setting something up that way.
i cant place my predictions on who would win, because i dont know you personally. but on TUF 10, kimbo still has to work on his ground game, and improve slight flaws in his striking. but like the first commentor said, you can contact American Top Team