Osteochondral defects are defects of both cartilage and underlying subchondral bone, typically affecting weightbearing joints such as the ankle and knee. Defects can occur through acute trauma, natural wear and tear of the joint, or underlying diseases of the bone. The mechanism of osteochondral defect repair is elusive, with inconsistency in how healing occurs in various animal models and no golden standard surgical treatment currently available. Lydon et al hypothesise osteochondral defects in ovine models heal via endochondral ossification. We present a mathematical model of osteochondral defect regeneration to validify the underlying mechanisms of healing. Our mathematical model replicates this endochondral ossification process, with stages of healing regulated by growth factors, highlighting their important role in the successful healing of an osteochondral defect. Our model successfully shows cartilage formation followed by matrix calcification and conversion into bone.