Tears of the peroneal tendons are not uncommon but remain an underappreciated source of chronic lateral ankle pain. The purpose of this study was to identify the typical patient profile and nature of the injury, to analyze the course of treatment, and to determine the prevalence of complications seen with surgical repair. Forty patients with chronic pain over the peroneal tendons from the Foot and Ankle Institute at the Western Pennsylvania Hospital underwent peroneal tendon repair. During a 3-year period, a retrospective review was performed by evaluating medical records, surgical reports, and radiographs. The average patient age was 42 years (range, 13 to 64 years). The most common cause was an ankle sprain or other traumatic injury (58%). Peroneus brevis tears (35 patients; 88%), peroneus longus tears (5 patients; 13%), combined peroneus brevis and longus tears (15 patients; 37%), low-lying peroneus muscle belly (13 patients; 33%), lateral ankle ligamentous disruptions (13 patients; 33%), and peroneal subluxation (8 patients; 20%) were identified during surgery. The average follow-up was 13 months (range, 9 to 40 months). Ninety-eight percent of the patients were able to return to full activities without pain at final follow-up. The minor complication rate (transient symptoms) was 20%. Clinically significant (major) complications (continued symptoms or revisionary surgery) occurred in 10% of patients. This study indicates that lateral ankle ligamentous incompetence, combined peroneal brevis and longus tears, and low-lying peroneus muscle belly commonly coexist in patients with peroneal tendon injuries. Appropriate surgical intervention of peroneal tendon tears and their coexisting pathology yields successful and predictable results with few clinically significant complications.