Teeth trauma has become one of the most serious physical problems that people are suffering from in the past years. Early diagnosis and management are desperately needed to improve tooth survival, functionality and avoid the tooth loss. However, the diagnosis of cracked tooth could be challenging due to the small size of the crack. Therefore, a mechanics understanding of the tooth fracture is demanding from the perspective of developing a framework for failure prediction in clinical research and bio-mimetic restorative materials. This study focuses on characterising the anisotropic fracture behaviour and the crack shielding mechanisms in elephant dentin. This is often used as a structural analogue for human dentin due to the similarities in microstructure and chemical composition, in order to avoid the test-piece size restrictions, given the larger size of ivory than human teeth. Compact tension test-pieces were extracted from different locations on the ivory tusk so as to have different crack growth directions relative to the microstructure to inspect the fracture anisotropies. The fracture toughness as a function of the crack extension was assessed in terms of fracture resistance curves (R-curve). The accumulative crack-tip strain fields were also measured for the first time in dentin using digital image correlation technique (DIC) to investigate the capability of crack-tip elastic/plastic deformation before material failure. Investigation of crack morphologies, the interaction between crack and the microstructures, the fracture surfaces using both 2-D and 3-D techniques could provide with insights into extrinsic shielding mechanisms. Surface and volume crack opening displacement (COD) were measured for the first time optically and by X-ray computed tomography to investigate the effect of extrinsic crack-tip shielding. The displacement fields around the crack-tip obtained by DIC were fitted using Westergaard's analytical solution to extract the effective stress intensity factor, by comparing this to the applied load, the efficiency of the crack-tip shielding could be evaluated. A novel cohesive element model (traction-separation law) was then established based on the COD results to simulate the physical process of crack-tip shielding. It is the first time the cohesive model has been adapted to studying the direct crack behaviour measured by in-situ experiment to predict the crack growth. This model was then validated using the crack-tip strain field and R-curve obtained from the experiment measurement.