Lateral ankle pain is a common clinical presentation having several important causes, including lateral ligament injury, peroneal tendon injury, sinus tarsi syndrome, and nerve entrapments. However, other causes should be kept in mind in patients with unusual patterns of pain or intractable symptoms. We present a review of common and some unusual causes of lateral ankle pain including a review of post-operative imaging findings following surgery for lateral ankle ligament and peroneal tendon injuries.