Osteochondral defects resulting from trauma or degenerative diseases are challenging to treat owing to the complex hierarchical structure and limited self-healing capacity of articular cartilage. Recent advancements have identified SOX9-positive sclerotomal progenitors (scl-progenitors), derived from human pluripotent stem cells (hPSCs), as a promising cell source capable of recapitulating endochondral ossification and promoting osteochondral regeneration. A personalized 3D bioprinted scaffold was developed using treated dentin matrix (TDM)—a decellularized matrix rich in low-crystallinity hydroxyapatite, type I collagen, and osteoinductive factors—as the core bioactive material. To enhance mechanical strength and printability, TDM was combined with methacrylated gelatin (GelMA) and zirconia nanoparticles (ZrO₂). SOX9+ scl-progenitors were encapsulated within the hydrogel matrix and printed using extrusion-based 3D bioprinting to fabricate cell-laden scaffolds with tunable biomechanical and biological properties. The engineered constructs supported robust cell viability, proliferation, and differentiation toward osteochondral lineages in vitro. In vivo implantation in a Nude-Rat knee osteochondral defect model demonstrated excellent biocompatibility and significant regeneration of both cartilage and subchondral bone tissue. This study presents a translatable and customizable platform integrating stem cell technology, natural biomaterials, and 3D bioprinting for osteochondral tissue engineering. The bioengineered construct offers substantial advantages for personalized osteochondral defect repair compared to conventional approaches.