Coastal areas typically have high social and economic development and are likely to suffer huge losses due to tropical cyclones. These cyclones have a great impact on the transportation network, but there have been a limited number of studies about tropical-cyclone-induced transportation network functional damages, especially in Asia. This study develops an innovative measurement and analytical tool for highway network functional damage and risk in the context of a tropical cyclone, with which we explored the critical spatial characteristics of tropical cyclones with regard to functional damage to a highway network by developing linear regression models to quantify their relationship. Furthermore, we assessed the network's functional risk and calculated the return periods under different damage levels. In our analyses, we consider the real-world highway network of Hainan province, China. Our results illustrate that the most important spatial characteristics were location (in particular, the midlands), travel distance, landfalling status, and origin coordinates. However, the trajectory direction did not obviously affect the results. Our analyses indicate that the highway network of Hainan province may suffer from a 90% functional damage scenario every 4.28 years. These results have critical policy implications for the transport sector in reference to emergency planning and disaster reduction.