Background: Cartilage degeneration is a common issue in patients with chronic lateral ankle instability. However, there are limited studies regarding the effectiveness of lateral ligament surgery on preventing talar and subtalar joint cartilage from further degenerative changes. Purpose: To longitudinally evaluate talar and subtalar cartilage compositional changes using magnetic resonance imaging T2* mapping in anatomic anterior talofibular ligament (ATFL)–repaired and ATFL-reconstructed ankles and to compare them with measures in asymptomatic controls. Study Design: Cohort study; Level of evidence, 3. Methods: Between January 2015 and December 2016, patients with chronic lateral ankle instability who underwent anatomic ATFL repair (n = 19) and reconstruction (n = 20) were prospectively recruited. Patients underwent 3.0-T magnetic resonance imaging at baseline and 3-year follow-up. As asymptomatic controls, 21 healthy volunteers were recruited and underwent imaging at baseline. Talar dome cartilage was divided into (1) medial anterior, central, and posterior and (2) lateral anterior, central, and posterior. Posterior subtalar cartilage was divided into (1) central talus and calcaneus and (2) lateral talus and calcaneus. Ankle function was assessed using the American Orthopaedic Foot & Ankle Society scores. Results: There were significant increases in T2* values in medial and lateral posterior and central talus cartilage from baseline to 3-year follow-up in patients who underwent repair. T2* values were significantly higher in ATFL-repaired ankles at follow-up for all cartilage regions of interest, except medial and lateral anterior and lateral central, compared with those in healthy controls. From baseline to 3-year follow-up, ATFL-reconstructed ankles had a significant increase in T2* values in lateral central and posterior cartilage. T2* values in ATFL-reconstructed ankles at follow-up were elevated in all cartilage regions of interest, except medial and lateral anterior, compared with those in healthy controls. ATFL-repaired ankles showed a greater decrease of T2* values from baseline to follow-up in lateral calcaneus cartilage than did ATFL-reconstructed ankles ( P = .031). No significant differences in American Orthopaedic Foot & Ankle Society score were found between repair and reconstruction procedures (mean ± SD, 19.11 ± 7.45 vs 16.85 ± 6.24; P = .311). Conclusion: Neither anatomic ATFL repair nor reconstruction could prevent the progression of talar dome and posterior subtalar cartilage degeneration; however, ankle function and activity levels were not affected over a short period. Patients who underwent ATFL repair exhibited lower T2* values in the lateral calcaneus cartilage than did those who underwent reconstruction.