The typhoon wind characteristics designing for buildings or bridges located in complex terrain and typhoon prone region normally cannot be achieved by the very often few field measurement data, or by physical simulation in wind tunnel. This study proposes a numerical simulation procedure for predicting directional typhoon design wind speeds and profiles for sites over complex terrain by integrating typhoon wind field model, Monte Carlo simulation technique, CFD simulation and artificial neural networks (ANN). The site of Stonecutters Bridge in Hong Kong is chosen as a case study to examine the feasibility of the proposed numerical simulation procedure. Directional typhoon wind fields on the upstream of complex terrain are first generated by using typhoon wind field model together with Monte Carlo simulation method. Then, ANN for predicting directional typhoon wind field at the site are trained using representative directional typhoon wind fields for upstream and these at the site obtained from CFD simulation. Finally, based on the trained ANN model, thousands of directional typhoon wind fields for the site can be generated, and the directional design wind speeds by using extreme wind speed analysis and the directional averaged mean wind profiles can be produced for the site. The case study demonstrated that the proposed procedure is feasible and applicable, and that the effects of complex terrain on design typhoon wind speeds and wind profiles are significant.