The initial diagnosis of an "ankle sprain" is not always correct. Prolonged pain, swelling and disability sufficient to limit the activity and refractory to treatment following an ankle injury are not typical of an ankle sprain and should alert the clinician of the possibility of an alternative or an associated diagnosis. There are several conditions that can be misdiagnosed as an ankle sprain and those include ankle syndesmosis injuries, sinus tarsi syndrome, ankle and hind foot fractures, osteochondral lesions, posterior tibialis and peroneal tendons abnormalities, spring ligament damage, impingement syndromes and reflex sympathetic dystrophy. In this review, we discuss the imaging features of these conditions that can clinically mimic an ankle sprain. It is crucial to remember that unresolved ankle pain following an injury is not always just due to a "sprain".