This case report is about the rare combination of a concomitant ipsilateral occurrence of traumatic Achilles tendon rupture (ATR) and medial malleolar fracture (MMF) in a 59-year-old male patient. We have conducted a literature review and found 12 published cases on the same topic with similar trauma mechanism and characteristic clinical findings. Nevertheless, either the ATR or the MMF was missed in the initial clinical examination in two-thirds of the reported cases. In this case report we discuss the trauma mechanism and clinical findings of ATR and MMF and aim to increase the awareness of the combination of both injuries.