The demand of energy from our society is rapidly increased year on year linear to the world economic growth. Ocean gives great energy potential resources to fulfill energy need. For instance, oil and gas exploitation activities in offshore field had been established for a long time. Thus, such kind of operation should be improved in manner of safety to achieved global economy goal for a cleaner, safer, and sustain of the ocean. One of the process during oil and gas exploitation is cargo loading and offloading from shipto-ship. Due to consider as dangerous goods, oil and gas cargo transfer process is obligated to fulfill several safety criteria. A ship-to-ship configuration has more complex hydrodynamic-induced motion behavior than the single ship. Due to its complexity, a proper evaluation study is needed to evaluate a safety of the ship-to-ship operation. This simulation study is performed by Numerical Fluid Dynamic method in ideal fluid approach. In order to observe the complex hydrodynamic behavior, incident random wave is applied to side-by-side ships in different configuration by considering three mains steps during ship-to-ship operation i.e. berthing, moored, and un-berthing scenario. Criteria had been being evaluated are ships clearances, relative motion between ships, ships roll motion, forces acting on ships and tug boat, mooring lines loads and fenders deflection. Not only internal factor from the ships evaluated as safety criteria but also the external factor is evaluated. The external factor considered from weather are wind speed and wave height limitation.