The purpose of this study was to investigate the behavior of the tooth–bone interface on the nature of stress distribution in the tooth and its supporting alveolar bone for various occlusal loads using an advanced digital photoelastic technique. A digital image processing system coupled with a circular polariscope was used for the stress analysis. The phase shift technique and a phase unwrapping algorithm was utilized for fringe processing. This aids in obtaining qualitative and quantitative information on the nature of stress distribution within the dento-osseous structures. The experiments revealed bending stresses within dento-osseous structures. However, the compressive stress magnitude was larger than the tensile stress. Zero stress regions were also identified within the dento-osseous structures. The results suggest that the geometry of the dento-osseous structures and the structural gradients at the tooth–bone interface play a significant role in the distribution of stresses without stress concentrations. Further, the application of an advanced image-processing system with the circular polariscope showed notable advantages and could be applied in other biomechanical investigations.