Ankle injuries can lead to early osteoarthrosis when diagnosis is delayed. The clinical presentation of an osteochondral lesion of the talar dome is often difficult to diagnose in the initial setup of an ankle sprain or fracture. Once the lesion is adequately imaged and staged, open or arthroscopic treatment can be initiated. We discuss the arthroscopic treatment of a posteromedial talar dome lesion in this case report. Transmalleolar drilling was performed to treat an osteochondral lesion of the talar dome in a 24-year-old female. Her ankle evolved toward a severe clinical and radiologic condition in which a combined talar and tibial (kissing) lesion was seen during her follow-up. Therefore, we recommend the use of retrograde drilling or arthroscopic microfracture with minimal iatrogenic risk, instead of transmalleolar drilling, as the treatment of choice in these specific osteochondral lesion of the talar dome cases. (J Am Podiatr Med Assoc 99(1): 54–57, 2009)