This study develops a probability-based methodology to evaluate dam overtopping probability that accounts for the uncertainties arising from wind speed and peak flood. A wind speed frequency model and flood frequency analysis, including various distribution types and uncertainties in their parameters, are presented. Furthermore, dam overtopping probabilities based on monthly maximum (MMax) series models are compared with those of the annual maximum (AMax) series models. An efficient sampling scheme, which is a combination of importance sampling (IS) and Latin Hypercube sampling (LHS) methods, is proposed to generate samples of peak flow rate and wind speed especially for rare events. Reservoir routing, which incorporates operation rules, wind setup, and run-up, is used to evaluate dam overtopping probability.