Background: Multiple ankle pathologies have been found to coexist with chronic lateral ankle ligament instability, but their prevalence varies widely in the literature. The purpose of this study is to reexamine the prevalence of these associated pathologies and to determine their impact on reoperation rate. Methods: We retrospectively reviewed 382 cases of lateral ankle ligament repair/reconstruction between June 2006 and November 2016. Patient charts and radiograph reports were examined for the presence of any associated foot and ankle pathologies as well as clinical course. The effect of copathologies on reoperation rate was examined using binary logistic regression and the χ2 test. Results: We included a total of 99 cases. Copathologies included peroneal pathology (75/99, 75.8%), ankle impingement (40/99, 40.4%), and osteochondral lesion of the talus (17/99, 17.2%); 36.4% (36/99) had a low-lying muscle belly of peroneus brevis. The total reoperation rate was 12/92 (13.1%). It was lower in cases with peroneal pathology (8.7% vs 27.5%, P =.032). Conclusion: Peroneal pathology, ankle impingement, and osteochondral lesions were the most common associated copathologies in surgical patients with chronic lateral ankle ligament instability. The presence of peroneal pathology may lead to fewer reoperations, possibly as a result of a more comprehensive first-time surgical approach. Level of Evidence: Level III: Retrospective cohort.