The objective of this research was to determine the probability of road overtopping occurrence for a road culvert caused by surface runoff from the upstream catchment. A hydrological–hydraulic model was used for the development of an algorithm for road culvert maintenance based on the overtopping occurrence probability (CMOOP algorithm) for small mountain catchments. The hydrological model defines the regression dependence between the runoff hydrograph peak values and the probability of occurrences, whereas the hydraulic model calculates the culvert flow capacity by including in the calculation the level of sediment that culvert is filled with. The relationship between occurrences of overtopping and peak runoff value was defined using the runoff hydrograph transformation model in the accumulation on the upstream side of the road. In addition to the calculation of overtopping occurrence probability for the existing culvert condition, the CMOOP algorithm was used to analyze the impact of rehabilitation and reconstruction works from the perspective of legally based safety criterion for road overtopping occurrence probability (SCROOP). The CMOOP algorithm was appled to 67 concrete culverts located in a mountain road section in the Republic of Serbia. The results show that the application of rehabilitation works on selected culverts will increase the percentage of culverts that satisfy SCROOP from 49.25% to 89.55%, which confirms that the accumulated stone sediment is the main reason for the SCROOP unfulfillment.