Athletic disorders of the flexor hallucis longus (FHL) tendon primarily afflict dancers and tend to be overuse injuries. The commonest symptom is posteromedial ankle pain, arising from FHL disease in the unyielding fibro-osseous tunnel at the posterior talus. Less common sites are the knot of Henry in the midfoot and intersesamoid area in the forefoot. A high degree of suspicion is necessary to distinguish FHL pathology from co-existing clinical entities, since the FHL is intimately related with various other structures in its course. Conservative treatment focuses on FHL stretching exercises. Surgery is reserved for athletes with debilitating symptoms refractory to nonoperative measures. Open and arthroscopic approaches each have advantages and disadvantages, however no consensus exists regarding the superiority of one over the other. Rehabilitation cornerstones are neuromuscular re-education, rectifying faulty sport technique, and physical conditioning to minimize recurrence.