Natural human tooth consists of multiple layered quasi-brittle biomaterials, which make dental restorations experience a complex stress state under masticatory contact loading. As such, many restorations are prone to failure and a constant effort is made to improve the mechanical characteristics of the restorative materials. Clinical observations have shown that improved strengths and fracture toughness in ceramic materials do not necessarily lead to an anticipated higher functional longevity of the restoration. While substantial experimental investigations have been carried out to identify the contact induced fracture in such multi-layer material systems, numerical modelling of this event was largely unexplored. This paper presents a new numerical method to account for micro-damage driven fracture in various multi-layered biomaterial structures. In this study, a Rankine constitutive model is adopted and the crack initiation and propagation are automatically implemented in an explicit finite element (FE) framework. The effects of indenter radius, surface curvature and thickness of layered biomaterials on the cracking patterns are investigated. The results show good agreement with the experimental studies in literature.