Medial malleolar osteotomy has been widely performed for posteromedial osteochondral lesions of the talus (OLT) to expose the lesion. In osteochondral fragment fixation, bioabsorbable pins should be inserted as perpendicular as possible to obtain the rigid fixation. However, the exposure of the lesion may depend on the osteotomy angle, which affects the pin insertion angles. This study aimed to analyze the relationship between pin insertion and osteotomy angles in the medial malleolar osteotomy. Twenty-four ankles of 23 patients were included. The malleolar bisector angle which was calculated from radiographs and actual osteotomy angles were measured on radiographs, and the pin insertion and osteotomy angles were measured using MRI. The intersection angle was defined by the tangential line of the tibial plafond and medial malleolar articular facet, and the bisector of this angle was defined as the malleolar bisector angle. The relationship between pin insertion and osteotomy angles was analyzed. There was no significant difference between the actual osteotomy (55.7° ± 6.6°) and malleolar bisector angles (57.4° ± 4.3°) on the radiograph. There was a significant correlation between pin insertion and osteotomy angles (rs = 0.601). The pin insertion angle (54.3° ± 5.9°) in the lower actual osteotomy angle than the malleolar bisector angle was smaller than those in the higher actual osteotomy angle (63.4° ± 8.2°). This study showed the osteotomy angle affected pin insertion angle. The osteotomy angle should not be smaller than the malleolar bisector angle at medial malleolar osteotomy to insert pins as perpendicular as possible for fixation of posteromedial OLTs. Copyright © 2022 The Japanese Orthopaedic Association. Published by Elsevier B.V. All rights reserved.