Based on probabilistic time-geography, the encounter between two moving objects is random. The quantitative analysis of the probability of encounter needs to consider the actual geographical environment. The existing encounter probability algorithm is based on homogeneous space, ignoring the wide range of obstacles and their impact on encounter events. Based on this, this paper introduces obstacle factors, proposes encounter events that are constrained by obstacles, and constructs a model of the probability of encounters of moving objects based on the influence of obstacles on visual perception with the line-of-sight view analysis principle. In realistic obstacle space, this method provides a quantitative basis for predicting the encountering possibility of two mobile objects and the largest possible encounter location. Finally, the validity of the model is verified by experimental results. The model uses part of the Wuhan digital elevation model (DEM) data to calculate the encounter probability of two moving objects on it, and analyzes the temporal and spatial distribution characteristics of these probabilities.