A field monitoring program on an experimental low-rise building with gable roof has been established and implemented at a typhoon-prone area in China. This paper presents the field measurements obtained during two tropical cyclones in 2009. The characteristics of near-ground winds during the tropical cyclones are reported and discussed, including wind velocity spectra and profiles of mean wind speed, turbulence intensity, and turbulence integral length scale. This paper focuses on analysis of the external surface pressures measured on the central cross section of the gable roof for winds normal to the ridgeline. Pressure coefficients, probability density functions, and power spectra of the measured wind pressures are analyzed in detail. In addition, wind tunnel experiment of pressure measurements on a 1:50-scaled model of the experimental building is conducted. Comparison of the field measurements and the model test results is then performed. The paper aims to provide reliable fullscale measurements for further understanding of wind pressures on the roof of a typical low-rise building during tropical cyclones and as benchmarks for comparisons with wind tunnel experimental and numerical simulation results.