The berthing/deberthing manoeuvring operation is the peculiar work owned to the marine pilot and the dock master. So, in the port or the shipyard, the berthing/deberthing manoeuvring operation requires considerable concentration and bears dangerousness. In that situation, a tug utilization is getting increased and the external forces have an effect on the own ship because of moving with low advance speed. In this study, we constructed the 2-dimensional virtual ship manoeuvring simulator system with which we can carry out the berthing/deberthing manoeuvring operation by using tugs in the external forces such as strong wind. And then, we propose the objective indexes by which the degree of manoeuvring difficulty evaluated. Using the present system, we carry out manoeuvring simulation experiment in order to grasp correlation between the objective indexes proposed here and the def{ree of manoeuvring difficulty felt by operator. Lastly, we discuss the evaluation technique of manoeuvring difficulty.