Anterior or anterior-lateral dislocation of the ankle is a rare condition that can be treated conservatively as well as any other similar types of ankle dislocations without associated fractures. We present a case report of an anterior-lateral ankle dislocation with a concomitant avulsion injury of the ankle's anterior capsule in a diabetic patient that was treated conservatively. At the patient's visit 12 months after the initial injury, he was asymptomatic with full range of motion of the ankle joint. To our knowledge, we could not identify this type of an injury in a diabetic patient that was treated successfully with conservative treatment in the existing literature.