Sharks and rays have distinctive skeletons among vertebrate animals, consisting primarily of unmineralized cartilage wrapped in a surface tessellation of minute polygonal tiles called tesserae, linked by unmineralized collagenous fibers. The discrete combination of hard and soft tissues is hypothesized to enhance the mechanical performance of tessellated cartilage (which performs many of the same functional roles as bone) by providing either rigidity or flexibility, depending on the nature of the applied load. These mechanisms and the effect of tesserae ultrastructure on cartilage mechanics, however, have never been demonstrated in the actual tissue, nor in bio-accurate models. In this study, we developed bio-inspired three-dimensional tesserae computer models, incorporating material properties and ultrastructural features from natural tessellated cartilage. The geometries of ultrastructural features were varied parametrically, and the effective modulus of whole tesserae was evaluated using finite element analysis to determine the roles of ultrastructural features in mechanics. (Jayasankar et al. 2020. Multi-scale modeling and mechanical performance characterization of stingray skeleton-inspired tessellations. Journal of the Mechanics and Physics of Solids, 138, 103906.)