Wheelset–rail rolling contact is more complex on curved track than on tangent track and is susceptible to rolling contact fatigue (RCF). This study presents an investigation of Belgrospi-like damage, features crack nests grouped periodically with short-pitch corrugation, which is a particular type of RCF that occurred on low rail of sharp curved track in a metro line in China. A 3D elastic–plastic wheelset–rail rolling contact model on curved track is developed using the finite element (FE) method to investigate the frictional rolling contact behavior with short-pitch corrugation. Emphasis is placed on solving detailed dynamic contact solutions, and inferring the consistent and differential relationships between them and the corrugation geometry to further analyze the causes of Belgrospi-like damage. It is found that the wheelset–rail frictional rolling contact induced by short-pitch corrugation is more likely to damage under rolling–slip conditions on low rail of sharp curved track. Consistent patterns of high dynamic vertical and longitudinal contact forces, Von-Mises stress, contact pressure, and surface shear stress are subjected to be responsible for Belgrospi-like damage initiation before the crest. The causes of Belgrospi-like damage were initially estimated, but need to be further monitored to prevent their development from affecting railway operations and maintenance.