Osteochondral lesions of the talus (OLTs) are a common clinical entity encountered by the foot and ankle surgeon. OLTs result from overuse and/or traumatic injury with subsequent alteration in the vascularity and structure of articular cartilage and subchondral bone. Although OLTs may be incidental findings in some cases, the clinical manifestations of symptomatic OLTs include significant pain, limited range of motion, and difficulty in performing activities of daily living and participating in recreational or competitive sports. The management of OLTs remains challenging, and several surgical techniques have been described, including marrow-stimulating methods, osteochondral autograft or allograft transplantation, and autologous chondrocyte implantation. Retrograde drilling is recommended for cases with intact overlying articular cartilage and subchondral insufficiency. With the advent of biological agents to enhance the natural healing response, techniques for treatment of OLTs are concurrently evolving. This article aims to describe a novel technique of retrograde drilling using a cannulated screw as a means to treat OLTs and using the screw guide wire as an insertion rod for the local delivery of an orthobiologic agent.