Pre-stressing in concrete railway sleepers yields endurance property under high-cycle fatigue. This structural effect plays a positive role in durability of the sleepers. However, as a common practice, track engineers often generate holes or web openings in concrete sleepers to enable the accommodation of rail equipment cables and signaling equipment. This study aims to provide a principle understanding of the structural capacity and energy toughness of pre-stressed concrete sleepers with and without holes and web openings. It will investigate the design criteria and effects of holes and web openings on the structural capacity of concrete sleepers under rail loading. The finite element modelling for ultimate strength design of concrete sleepers will be highlighted in this study. Static experimental investigations have been firstly carried out to validate the finite element models using ABAQUS. The models are capable of predicting the failure planes and can help provide practical guidelines for the holes and web opening for track engineers.