This paper describes Three-Dimensional Listening Simulation System (3D-LSS) which is to analyze whistle sound related marine casualties, and is to evaluate the accident situations using 3D sound by Head Related Transfer Function At first, the hree-dimensional listening model from the analysis of accident situations is proposed, and then the reproduction and evaluation methods of 3D sounds are also discussed. The system is designed to explain the accident situations and to simulate the possible situations with GUI based graphics and 3D sound reproduction. The evaluation experiments using 3D-LSS are carried out with six cases that did not known whether it is true or not the blast and listening of the whistle sound between two vessels. As results of psychological assessments by five subjects, the six cases can be analyzed clearly by visual images and audio sounds, thus the usability of 3D-LSS as one of the judgment assistant system of marine casualty is verified.