Biofabrication allows the formation of 3D scaffolds through a precise spatial control. This is of foremost importance when aiming to mimic heterogeneous and anisotropic architecture, such as that of the osteochondral tissue. Osteochondral defects are a supreme challenge for tissue engineering due to the compositional and structural complexity of stratified architecture and contrasting biomechanical properties of the cartilage-bone interface. This review highlights the advancements and retreats witnessed by using developed bioinks for tissue regeneration, taking osteochondral tissue as a challenging example. Methods, materials and requirements for bioprinting were discussed, highlighting the pre and post-processing factors that researchers should consider towards the development of a clinical treatment.