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.