Syndesmotic disruption occurs in more than 10% of ankle fractures. Operative treatment with syndesmosis screw fixation has been successfully performed for decades and is considered the gold standard of treatment. Few studies have reported the long-term outcomes of syndesmosis injuries. This study investigated long-term patient-reported, radiographic, and functional outcomes of syndesmosis injuries treated with screw fixation and subsequent timed screw removal. A retrospective cohort study was carried out at a Level I trauma center. The study group included 43 patients who were treated for ankle fractures with associated syndesmotic disruptions between December 2001 and May 2011. The study included case file reviews, self-reported questionnaires, radiologic reviews, and clinical assessments. At 5.1 (±1.76) years after injury, 60% of participants had pain, 26% had degenerative changes, 51% had loss of tibiofibular overlap, and 33% showed medial clear space widening. Retained syndesmotic positions on radiographs were linked to better self-reported outcomes. There is an inversely proportional relation between age at the time of injury and satisfaction with the outcome of the ankle fracture as well as a directly proportional relation between age at the time of injury and pain compared with the preinjury state. Optimal restoration and preservation of the syndesmosis is crucial. Syndesmotic disruption is associated with poor long-term outcomes after ankle fracture. Greater age is a risk factor for chronic pain and dissatisfaction with the outcome of ankle fracture and syndesmosis injury. Therefore, patient education to facilitate realistic expectations about recovery is vital, especially in older patients.