The lateral ligament complex of the ankle is the most frequently injured structure in the body. Although most simple ankle sprains do not result in long-term disability, a significant number do not completely resolve, leading to residual symptoms that may persist for years. The most commonly reported symptoms, particularly among athletes, include instability, re-injury and tendinitis. Ballet dancers are a combination of artist and high-performance athlete; consequently, they are subjected to the same types of injuries as other athletes, including lateral ankle sprains and their sequelae. Furthermore, ballet dancers perform in unusual positions such as en pointe, which places the ankle in extreme plantar flexion, requiring stabilization by surrounding muscles. Dancers’ extraordinary performance demands place them at risk for other ankle injuries as well, including inflammation of several tendons, especially the peroneals. This report reviews the relevant literature to characterize the scope of lateral ankle sprains and sequelae, discuss the importance of the peroneal muscles in ankle stability, and explore a relationship between lateral ankle sprain and ankle tendinitis in ballet dancers. Informal interviews were conducted with physical therapists who specialize in treating ballet dancers, providing a clinical context for this report. An extensive review of the literature was conducted, including electronic databases, reference lists from papers, and relevant reference texts. Numerous studies have investigated ankle sprains and residual complaints; nearly all report that lateral ankle sprains commonly lead to chronic ankle instability. Studies exploring ankle stability have demonstrated that the peroneal muscles play a crucial role in ankle stabilization; EMC studies confirm they are the first to contract during ankle inversion stress. The dancers need for exceptional ankle stabilization may lead to peroneal overuse and tendinitis. Studies have linked peroneal pathology to a history of ankle sprain, but there is no dance medicine literature linking peroneal tendinitis to prior ankle sprains. A growing body of literature confirms myriad connections between lateral ankle sprains, residual instability, peroneal muscle increased activity, and tendinitis. It is our belief that ankle sprains lead to instability, particular en pointe, for which the peroneal muscles attempt to compensate. Their overuse for this static stabilizing function, as well as for dynamic dance movements, then leads to tendonitis. This knowledge may heighten awareness of the potential for developing tendonitis following ankle sprains, and lead to better rehabilitation of the injured ballet dancer.