Osborne-Cotterill lesion is an osteochondral fracture located in the posterolateral margin of the humeral capitellum, which may be associated with a defect of the radial head after an elbow dislocation. This lesion causes instability by affecting the lateral ulnar collateral ligament over its capitellar insertion, which is associated with a residual capsular laxity, thereby leading to poor coverage of the radial head, and hence resulting in frequent dislocations. We present a 54-year-old patient, a physician who underwent trauma of the left elbow after falling from a bike and suffered a posterior dislocation fracture of the elbow. The patient subsequently presented episodes of instability, and additional work-up studies diagnosed the occurrence of Osborne-Cotterill lesion. An open reduction and internal fixation of the bony lesion was performed, with reinsertion of the lateral ligamentous complex. Three months after surgery, the patient was asymptomatic, having a flexion of 130º and extension of 0º, and resumed his daily activities without any limitation. Currently, the patient remains asymptomatic 2 years after the procedure. Elbow instability includes a large spectrum of pathological conditions that affect the biomechanics of the joint. The Osborne-Cotterill lesion is one among these conditions. It is a pathology that is often forgotten and easily overlooked. Undoubtedly, this lesion requires surgical intervention.