PURPOSE: The aim of this study was to determine which intra-articular injuries are associated with chronic anterolateral pain and functional instability after an ankle sprain. METHODS: From 2008 to 2010, records of all patients who underwent ankle joint arthroscopy with anterolateral pain and functional instability after an ankle sprain were reviewed. A systematic arthroscopic examination of the intra-articular structures of the ankle joint was performed. Location and characteristics of the injuries were identified and recorded. RESULTS: A total of 36 ankle arthroscopic procedures were reviewed. A soft-tissue occupying mass over the lateral recess was present in 18 patients (50%). A partial injury of the anterior talofibular ligament (ATFL) was observed in 24 patients (66.6%). Cartilage abrasion due to the distal fascicle of the anteroinferior tibiofibular ligament coming into contact with the talus was seen in 21 patients (58.3%), but no thickening of the ligament was observed. Injury to the intra-articular posterior structures, including the transverse ligament in 19 patients (52.7%) and the posterior surface of the distal tibia in 21 patients (58.3%), was observed. CONCLUSION: Intra-articular pathological findings have been observed in patients affected by anterolateral pain after an ankle sprain. Despite no demonstrable abnormal lateral laxity, morphologic ATFL abnormality has been observed on arthroscopic evaluation. An injury of the ATFL is present in patients with chronic anterolateral pain and functional instability after an ankle sprain. A degree of microinstability due to a deficiency of the ATFL could explain the intra-articular pathological findings and the patients' complaints. LEVEL OF EVIDENCE: IV.