This paper presents the preliminary results from a project aimed to assess the mechanical behaviour of bamboo under various loading conditions. For this purpose, a number of bamboo ring specimens were prepared from dry moso bamboo, and were compressed in the radial direction. The plots of load versus displacement were recorded, and the failure process and modes are analysed. Corresponding to the experimental investigations, an FEA model is developed to simulate the stress/strain distribution and failure process of diametrical compressive tests of bamboo. The FEA model consists of multiple isotropic elastic layers to simulate the gradient structure of bamboo and the associated calculations were performed using ANSYS software. It is demonstrated that the simulated stress/strain fields in the bamboo and failure process agree well with the experimental observations and the Young’s modulus and strength estimated based on the experiments and FEA simulation are consistent with those reported in the literature.