Uncertainty associated with a sampling method is very high in evaluating the degree of site contamination; therefore, such uncertainty affects the reliability of precise investigation and remediation verification. In particular, in evaluating a site for a small-sized filling station, underground utilities, such as connection pipes and oil storage tanks, make grid-unit sampling impossible and the resulting increase in uncertainty is inevitable. Accordingly, this study quantified the uncertainty related to the evaluation of the degree of contamination by total petroleum hydrocarbon and by benzene, toluene, ethylene, and xylene. When planning a grid aimed at detecting a hot spot, major factors that influence the increase in uncertainty include grid interval and the size and shape of the hot spot. The current guideline for soil sampling prescribes that the grid interval increase in proportion to the area of the evaluated site, but this heightens the possibility that a hot spot will not be detected. In evaluating a site, therefore, it is crucial to estimate the size and shape of the hot spot in advance and to establish a sampling plan considering a diversity of scenarios.