Osteochondral defects present a significant clinical challenge due to the complex structural and functional integration required between articular cartilage and subchondral bone. Conventional treatments often fail to restore the native zonal architecture, resulting in fibrocartilaginous repair and long-term degeneration. Advances in three-dimensional (3D) bioprinting have introduced new opportunities to fabricate multiphasic, spatially organized scaffolds that better replicate the hierarchical gradients of osteochondral tissue. This chapter examines emerging bioprinting strategies—including extrusion-based, digital light processing, and multimaterial approaches—that enable precise control over scaffold geometry, mechanical properties, and biochemical cues. Emphasis is placed on the design of compartment-specific biomaterials and bioinks, gradient structures, and localized delivery of growth factors and bioactive ions to guide lineage-specific regeneration. Recent innovations in integration, immune-modulatory hydrogels, and cell-laden constructs are also discussed. Together, these developments underscore the transition from passive scaffolds to bioinstructive platforms capable of orchestrating spatially defined osteochondral tissue engineering (OCTE), thereby advancing clinical translation.