The purpose of this study was to examine a young athletic population to update the data regarding epidemiology and disability associated with ankle injuries. At the United States Military Academy, all cadets presenting with ankle injuries during a 2-month period were included in this prospective observational study. The initial evaluation included an extensive questionnaire, physical examination, and radiographs. Ankle sprain treatment included a supervised rehabilitation program. Subjects were reevaluated at 6 weeks and 6 months with subjective assessment, physical examination, and functional testing. The mean age for all subjects was 20 years (range, 17-24 years). There were 104 ankle injuries accounting for 23% of all injuries seen. There were 96 sprains, 7 fractures, and 1 contusion. Of the 96 sprains, 4 were predominately medial injuries, 76 were lateral, and 16 were syndesmosis sprains. Ninety-five percent had returned to sports activities by 6 weeks; however, 55% of these subjects reported loss of function or presence of intermittent pain, and 23% had a decrement of >20% in the lateral hop test when compared with the uninjured side. At 6 months, all subjects had returned to full activity; however, 40% reported residual symptoms and 2.5% had a decrement of >20% on the lateral hop test. Neither previous injury nor ligament laxity was predictive of chronic symptomatology. Furthermore, chronic dysfunction could not be predicted by the grade of sprain (grade I vs. II). The factor most predictive of residual symptoms was a syndesmosis sprain, regardless of grade. Syndesmosis sprains were most prevalent in collision sports. This study demonstrates that even though our knowledge and understanding of ankle sprains and rehabilitation of these injuries have progressed in the last 20 years, chronic ankle dysfunction continues to be a prevalent problem. The early return to sports occurs after almost every ankle sprain; however, dysfunction persists in 40% of patients for as long as 6 months after injury. Syndesmosis sprains are more common than previously thought, and this confirms that syndesmosis sprains are associated with prolonged disability.