The dispatching problem in container transportation field are classified as the pickup and delivery problems, which are highly complex issues that consider various conditions in the work-site operations. Therefore, this study suggests the automated dispatching based on genetic algorithm. To achieve this, diverse constraints considered in work-site operations are established. Besides, dispatching rules and phases for generating initial solution are suggested. In this study, it is meaningful that it could solve the problem which considered various assumptions and constraints. In the future study, performance evaluation of genetic algorithm compare to optimization model is presented. At the same time, applicability in real container transportation field is identified through experiment based on work-site operations' data.