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Ankle sprains in the athlete are one of the most common injuries, and syndesmosis or “high-ankle” sprains seem to being diagnosed at an increasing rate. As a result, there has been a heightened interest in recognizing and treating these difficult injuries on a timely basis, particularly in the athlete. Although the recognition and diagnosis of these injuries have improved, there still exists a paucity of information on optimal conservative and operative management. In this paper, a systematic review of the literature was conducted to provide an evidence-based rationale in the diagnosis and treatment of syndesmosis (high ankle) sprains in athletes. It is obvious from the low level of evidence available in the literature on this topic that a great deal of work is needed before conclusive statements regarding the management of these injuries can be made with confidence. The current diagnostic tests are not very specific. Because this is a spectrum of injury, there is a lot of variability in the time lost from sport. It is clear that we need a much more definitive diagnostic process for this injury that allows us to predict the severity of the injury, time loss from sport, and the treatment required.