Autologous osteochondral transplantation is an established surgical procedure for osteochondritis dissecans (OCD) of the knee, and has recently been applied in cases of advanced-staged OCD of the elbow. The elbow procedure; however, is more technically demanding than for the knee. One reason is the difficulties of perpendicular insertion of large-diameter osteochondral plugs to the humeral capitellum with a small, narrow operative field in the humeroradial joint. Furthermore, if the OCD lesion is located on the lateral site of the capitellum, the creation of recipient holes perpendicular to the joint surface is difficult due to the risk of damaging the lateral wall of the capitellum. To avoid such difficulties, we developed a new technique by which 6.5 and/or 8.5 mm diameter plugs are harvested from the ipsilateral knee, having an oblique cartilage surface relative to the long axis of the plugs. These are then inserted into the recipient holes which are created obliquely from the lateral and distal to medial and proximal directions in the capitellum at an angle complimentary to the harvested plugs. This technique allows easy insertion of large-diameter plugs into recipient holes in a restricted operative field, even if the OCD lesion is located in the lateral site.