The purpose of this study is to evaluate a simulation model of a stacking guidance system (SGS) with a roller guide applicable to the mobile harbor. The study used a small-scale model (1/20) made of wood with rollers in order to compare the dynamic analysis with experiment results. The law of similarity was applied for the validation of the scaled model. In order to construct a more realistic simulation model, the damping coefficient of the dynamic model was adjusted to 0.5 Ns/mm for the wood-to-wood contact condition based on the experimental results. Using this validated model, dynamic simulations were also carried out for containers of 20, 30, and 40 tons. The results showed that the reaction force of the roller guide was increased from 74.7 kN to 91.2 kN as the weight of container increased. For the design of a roller guide for SGS, the results obtained in this study can be used to reduce the reaction force by employing a rubber roller or a highly damped rotational joint.