Solitary ankle fracture or Achilles Tendon (AT) rupture might not be an uncommon injury. However, concomitant ipsilateral ankle fracture with AT rupture is rare. The present report discusses this rare combination. A 30-year-old female had fallen while rock climbing and sustained a closed fracture of the medial malleolus with an ipsilateral complete AT rupture. Most of the reported cases had similar patterns, not only in terms of history, but also in terms of a similar fracture pattern. This rare combination of orthopedic injuries tends to occur when an abrupt excessive force is applied to the forefoot, with subsequent ankle hyperextension or hindfoot inversion. Imaging studies are useful both for confirming the injuries and for medicolegal and research purposes. Definitive treatment of the AT rupture is usually surgical in young active patients. Concomitant malleolar fractures can be managed conservatively or surgically, depending on the fracture configuration and degree of displacement. The importance of a thorough clinical examination in assessing the musculoskeletal and neurovascular structures in ankle injuries cannot be overemphasized. Knowledge of these injury patterns is crucial to reducing the incidence of residual morbidity such as ankle and foot weakness and loss of motion.