Numerical modelling and analysis of three-dimensional multiple retrogressive landslides of Saint-Jude landslide in sensitive clay is conducted. The investigations of the three-dimensional effects in determining the extent of landslides are concerned. To accurately simulate the extremely large deformation caused by progressive soil failure, a special form of SPH formulation known as finite particle method (FPM) is adopted. A hypoelastic–plastic model with strain softening is implemented to capture the key feature of the mechanical behaviour of the sensitive clay in undrained condition. The multiple progressive failure process, the final run-out stretch, and the retrogression distance of the Saint-Jude landslide are compared quantitatively with the data from site investigation. Furthermore, three-dimensional effects and influences of various factors, including slope morphology and soil properties, are discussed for better understanding of the development of retrogressive landslides in sensitive soil.