Acute ankle and hindfoot injuries are common in athletes and typically are treated conservatively. Persistent pain that has not responded to appropriate conservative treatment and prevents the patient from returning to play is more problematic for the athlete and the treating sports clinician. Making a specific clinical and imaging diagnosis in these patients can be quite challenging. This article discusses the imaging evaluation of chronic ankle and hindfoot pain related to osseous and soft-tissue injuries in athletes. MR imaging is the preferred imaging modality in most of the presented cases.