Osteochondral lesions of the ankle are a more common source of ankle pain than previously recognized. Although the exact pathophysiology of the condition has not been clearly established, it is likely that a variety of etiological factors play a role, with trauma, typically from ankle sprains, being the most common. Technological advancements in ankle arthroscopy and radiologic imaging, most importantly magnetic resonance imaging, have improved diagnostic capabilities for detecting osteochondral lesions of the ankle. Moreover, these technologies have allowed for the development of more sophisticated classification systems that may, in due course, direct specific future treatment strategies. Nonoperative treatment yields best results when employed in select pediatric and adolescent patients with osteochondritis dissecans. However, operative treatment, which is dependent on the size and site of the lesion, as well as the presence or absence of cartilage damage, is frequently warranted in both children and adults with osteochondral lesions. Arthroscopic microdrilling, micropicking, and open procedures, such as osteochondral autograft transfer system and matrix-induced autologous chondrocyte implantation, are frequently employed. The purpose of this article is to review the history, etiology, and classification systems for osteochondral lesions of the ankle, as well as to describe current approaches to diagnosis and management.