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Two cases of osteochondral lesions of the proximal phalanx of the great toe at the interphalangeal joint are presented. This condition is characterized by pain, swelling, and tenderness at the interphalangeal joint. The roentgenographic characteristics resemble osteochondritis dissecans. Curettage and bone grafting to the lesion is effective. These conditions in adolescent soccer players may be caused by chronic repetitive overloading of the interphalangeal joint using soccer shoes with soft, supple, and narrow toe boxes.