Lateral ankle pain is common with overuse and sports-related injuries and may cause considerable morbidity. The differential diagnosis of lateral ankle pain is extensive. Disorders of the peroneal tendons should be an important consideration during interpretation of a routine ankle magnetic resonance imaging (MRI) or ultrasound (US). This article presents a review of the common causes of peroneal tendon pathology with particular reference to anatomy, US, and MRI features. The importance of dynamic evaluation with ultrasound is also emphasized.