Osteochondral (OC) defect repair remains a significant clinical challenge, with an urgent need for new therapeutics to prevent degenerative diseases such as osteoarthritis (OA). OA progressively degrades cartilage and subchondral bone tissue, ultimately causing irreversible OC tissue damage. Current clinical interventions have limited success in restoring native OC tissue, which has fueled growing interest in tissue engineering solutions. Scaffold-based engineering strategies have emerged as promising solutions, utilizing biomaterials with tailored physical and chemical properties to promote cartilage and bone tissue regeneration. Recent advances emphasize replicating the hierarchical structure of the OC unit and incorporating immunomodulatory elements to enhance regenerative outcomes. Scaffolds with and without the presence of cells, growth factors, and biologics have progressed to clinical trials and received approvals in Europe and the United States. This chapter will provide recent updates on OC engineered graft design, preclinical evaluation, and their bench-to-bedside translation.