Background: Very little is known about the true prevalence, etiology and predisposing factors for Haglund's Syndrome, possibly due to a lack of literature. Both conservative and surgical management in athletic and nonathletic populations have produced unpredictable results. Both require a prolonged recovery time (many months or years), although a lack of scientific literature, particularly for athletes and regarding conservative management exists. No controlled trials have been performed to determine the optimal methods of management. Aim: This case report and literature review aims to identify and discuss the challenges with the management of Haglund's Syndrome occurring in an elite athlete. Methods: A search of the literature was conducted using the PubMed database from 1980 to April 29 2006. Limits were set to English. The following key indexing terms were used: Haglund's, calcaneal exostosis, retroealeaneal bursitis. More recent literature was emphasized because it would better represent current management and knowledge of the condition. Results: Using the above search criteria captured a total of 153 citations (31 articles for Haglund's, 72 for calcaneal exostosis, 50 for retrocalcaneal bursitis). After removing duplicates and unrelated articles, 29 articles were sourced. Data abstraction was completed independently by one author. Emphasis was placed on literature related to athletes and not on specific details regarding surgical techniques. Other pertinent literature that added significantly to the knowledge and understanding of the condition, particularly relevant to athletes, not found on these databases was also sourced. Papers were retrieved in electronic or hard copy format from the Macquarie University Library, Sydney University Library, Melbourne University Library or personal library collections. Conclusions: Athletic activity may not be feasible with Haglund's Syndrome present and a full return to competition following surgery may be difficult, particularly for elite athletes. Management should emphasize early identification and definitive treatment, although an optimal treatment strategy is yet to be identified. Prolonged conservative treatment may exacerbate soft tissue damage, lengthen post-surgical rehabilitation and predispose complications. Conversely, surgery suffers poor predictability with regards to symptoms and return to sport and prolonged rehabilitation is required post-surgery.