Anterior mitral leaflet prolapse repair is a highly effective procedure, but despite excellent operative results still has an inferior long-term durability when compared to posterior leaflet repair. We analysed mitral repair durability in 74 consecutive patients operated for anterior leaflet prolapse between 2010 and 2021. Their pre- and postoperative clinical, echocardiographic data and repair durability as well, were compared with74 randomly assigned posterior leaflet prolapse patients who underwent valve repair during the same period. While groups were of similar age, patients with anterior leaflet prolapse had an inferior preoperative status in terms of functional reserve, atrial fibrillation, operative risk, ejection fraction and had more dilated left heart chambers as well. 1, 5, and 10-year freedom from repair failure was 87.1 ± 4.6%, 79.8 ± 6.5% and 50.7 ± 12.5% in the anterior, and 98.5 ± 1.5% respectively in the posterior leaflet group. Atrial fibrilation (hazard ratio [HR]5.365; 95%; confidence interval[CI] 1.093-26.324 p = .038) and left ventricle end-systolic diameter (HR 1.160 95%; CI 1.037-1.299 p = .010) independently predicted anterior leaflet repair failure. Receiver Operating Curve analysis established left ventricle end-systolic diameter ≤42 mm as a cut-off value associated with improved anterior leaflet repair durability. Accordingly, 10-year repair durability in a subset of patients, with preserved left ventricle end-systolic diameter (≤42 mm) was 86.4 ± 7.8%. Better long-term repair durability in patients with anterior mitral leaflet prolapse and preserved sinus rhytm and left-ventricle diameters justifies early reconstructive approach.