One of the most frequent causes of degradation and failure of quasi-brittle biomaterials is fracture. Mechanical breakdown, even when not catastrophic, is of particular importance in the area of biomaterials, as there are many clinical situations where it opens the path for biologically mediated failures. Over the past few decades the materials/biomaterials community has developed a number of numerical models, but only with limited incorporation of brittle failure phenomena. This article investigates the ability of a non-linear elastic fracture mechanics (NLEFM) model to reliably predict failure of biomaterials with a specific focus on the clinical settings of restorative dentistry. The approach enables one to predict fracture initiation and propagation in a complex biomechanical status based on the intrinsic material properties of the components. In this paper, we consider five examples illustrating the versatility of the present approach, which range from the failure of natural biomaterials, namely dentine and enamel, to a restored tooth, a three unit all ceramic bridge structure and contact-induced damage in the restorative layered materials systems. It is anticipated that this approach will have ramifications not only to model fracture events but also for the design and optimisation of the mechanical properties of biomaterials for specific clinically determined requirements.