Osteochondral sockets are formed using a retrograde drill assembly. The retrograde drill assembly includes a guide pin having a fluted tip and an externally threaded portion. A removable cutter head has internal threads that engage the threads of the guide pin. The guide pin is drilled through bone, exposing the external threads in a joint space requiring repair. The cutter is threaded onto the guide pin, and the assembly is retrograded with rotation to form a socket in the bone. The cutter is disengaged from the guide pin for disassembly and removal from the bone, making way for an implant to be installed in the pocket. The implant can be drawn into the socket using an attached strand threaded through the bone socket and out of the bone.