The purpose of this study was to evaluate the associations of the shape of the first metatarsal head with (1) the presence of osteoarthritis in the sesamoid-metatarsal joint and (2) the pronation angle of the first metatarsal head on foot radiographs. A total of 121 patients, with the mean age of 61 years, underwent weight-bearing dorsoplantar, lateral, and first metatarsal axial radiographs. The shape of the first metatarsal head's lateral edge was classified as either rounded, intermediate, or angular in shape in the dorsoplantar view. The presence of osteoarthritis in the sesamoid-metatarsal joint and the pronation angle of the first metatarsal head were assessed in the first metatarsal axial view. Other variables that could affect the first metatarsal shape, including the lateral first metatarsal inclination angle, were also assessed. Univariate and multivariate analyses were performed to determine the associations. The prevalence of sesamoid-metatarsal osteoarthritis was significantly higher (77%, 27%, and 29% for rounded, intermediate, and angular, respectively, P < .001), and the metatarsal pronation angle was significantly larger (14°, 8°, and 4° for rounded, intermediate, and angular, respectively, P < .001) in feet with a rounded metatarsal head. These associations were also significant in the multiple regression analysis. A rounded metatarsal head was associated with a higher prevalence of osteoarthritis within the sesamoid-metatarsal joint, as well as a larger first metatarsal head pronation angle. A negative round sign can be used as a simple indicator of an effective correction to the first metatarsal pronation angle during hallux valgus surgery. However, in feet with sesamoid-metatarsal osteoarthritis, surgeons will need to be cautious as overcorrection may occur. Copyright © 2019 The Japanese Orthopaedic Association. Published by Elsevier B.V. All rights reserved.