Despite huge efforts, tissue engineers and orthopedic surgeons still face a great challenge to functionally repair osteochondral (OC) defects. Nevertheless, over the past decade great progress has been made to find a suitable strategy towards OC regeneration. In the clinics, some osteochondral tissue engineering (OCTE) approaches have already been applied although with some incongruous outcomes as OC tissue is complex in its architecture and function. In this chapter, we summarize current OCTE strategies that are focused on hierarchical scaffold design, mainly layered scaffolds. Most suitable candidates towards functional regeneration of OC tissues are envisaged from monophasic to the layered scaffolds. Herein is documented a variety of approaches with their intrinsic properties applied as bare scaffolds or in combination with biologics, either in in vitro or in vivo evaluations aiming at functional OC regeneration. The most noteworthy studies in OC regeneration developed within the past 5 years are documented as well as some that are currently undergoing clinical trials.