In this paper, we present a method to assess the influence of the initial reservoir level in hydrological dam safety and risk analysis. Traditionally, in professional practice, the procedures applied are basically deterministic. Several physical processes are defined deterministically, according to the criteria of the designer (usually in the conservative side), although there is a high degree of uncertainty regarding these processes. A relevant variable is the reservoir level considered at the beginning of flood events. Hydrological dam safety assessment methods traditionally assume that the reservoir is initially full when it receives the design flood, thus, staying in the conservative side when designing a new dam. However, the distribution of reservoir levels at the beginning of flood episodes takes more importance for evaluating the real risk for the dams in operation. We analyzed three different scenarios—initial reservoir level equal to maximum normal level, equal to a maximum conservation level, and following the probability distribution from the historical records. To do so, we presented a method applied to a gated-spillway dam located in the Tagus river basin. A set of 100,000 inflow hydrographs was generated through a Monte Carlo procedure, by reproducing the statistics of the main observed hydrograph characteristics—peak flow, volume, and duration. The set of 100,000 hydrographs was routed through the reservoir applying the Volumetric Evaluation Method as a flood control strategy. In order to compare the three scenarios, we applied an economic global risk index. The index combines the hydrological risk for the dam, linked to the maximum water level reached in the reservoir, during the flood routing, and the flood risk in the downstream river reach, linked to the discharge releases from the dam. The results showed the importance of accounting for the fluctuation of initial reservoir levels, for assessing the risk related to hydrological dam safety. Furthermore, a procedure to quantify the uncertainty associated with the effects of initial reservoir level on hydrological dam safety, has been proposed.