The medial patello-femoral ligament (MPFL) is considered the primary restraint against patellar dislocation and its reconstruction is indicated in recurrent patellar instability. An anatomical positioning of MPFL femoral insertion is recommended to achieve satisfactory clinical outcomes and prevent osteoarthritis (OA) due to an altered kinematics. The purpose of the study was first to assess the relationship between correct femoral tunnel position and better clinical outcomes and lower patellofemoral osteoarthritis rate. Second, correlation of outcomes with factors potentially affecting the results, such as the type of graft, patellar height and trochlear dysplasia. Fifty-three patients (58 knees) who underwent MPFL reconstruction between 2009 and 2018 by a senior knee surgeon were retrospectively evaluated. Knee radiographs were performed before surgery, 12 months later and at last follow-up to assess trochlear dysplasia, patellar height and patellofemoral OA. The tibial tuberosity-trochlear groove (TT-TG) value was measured on a CT scan. The accuracy of graft positioning was evaluated on sagittal radiographs according to Schöttle et al. Subjective outcomes were collected before surgery, at 12 months and at last follow-up using several validated scores. Forty-six patients (51 knees) with a mean age of 24.1 ± 7.4 years were included in the study. Mean follow-up was 8.9 ± 2.1 years. A significant improvement in all clinical scores was observed at 12 months and final follow-up. Anatomic Insertion (AI) of reconstructed MPFL was considered optimal in 33 (64.7%) and sub-optimal in 18 (35.3%) patients. Sub-optimal AI resulted in lower Kujala, IKCD and higher VAS score (p < 0.01); moreover, for every 1 mm distance in any direction from the ideal insertion, a decrease of 0.8 [95% CI (-1.4; -0.2)] in Kujala score and 0.8 [95% CI (-1.3; -0.3)] in IKDC was observed. At final follow-up, 8 patients presented patellofemoral OA Iwano grade 3 (15.7%): although that incidence did not correlate to graft positioning, the use the artificial ligament in all these cases appeared to be significant. The present study confirms the importance of an optimal anatomic femoral insertion in MPFL reconstruction, reporting a significant positive correlation between graft positioning and clinical outcome. No significant correlations were found between anatomic insertion and patello-femoral OA development. IV. © 2022. The Author(s) under exclusive licence to European Society of Sports Traumatology, Knee Surgery, Arthroscopy (ESSKA).