Background: Measuring the chordae tendineae for mitral valve reconstruction is feasible with various techniques. However, the effect of different strategies on the durability of plastics at follow-up is unknown. The study aims to compare a conventional surgical technique for measuring artificial chordae length with our new approach, defined “track technique”. Methods: We compared the results of patients with anterior leaflet prolapse/flail who underwent mitral valve reconstruction by implanting artificial chordae from January 2020 to January 2022; 22 patients were operated on with a conventional technique, and 25 with our new alternative, “track technique”. Clinical and transesophageal echocardiography data were collected postoperatively and at 2 years of follow-up. The primary outcome was freedom from mitral regurgitation. Secondary outcomes were presentation with New York Heart Association (NYHA) class 2 and leaflet coaptation length \ge10 mm. Results: The patients of the 2 groups had comparable preoperative risk factors regarding the LogEuroSCORE (p = 0.33). Moreover, no difference was observed in terms of the mechanism of mitral valve insufficiency. No hospital or follow-up deaths were recorded for either group. At discharge, no echocardiographic differences were observed in the regarding degree of residual mitral regurgitation, but the measurement of coaptation length was in favor of the alternative group (8.6 \pm 1.8 vs. 11 \pm 1.4; p = 0.04). At 2 years of follow-up (25 \pm 9; range 13–37), the NYHA class was not different; however, the number of patients with 1–2+ recurrent mitral regurgitation was significantly higher in the conventional group (8 vs. 4 patients; p = 0.02), and the coaptation length was in favor of the alternative group (8.8 \pm 1.7 vs. 11 \pm 1.7; p = 0.04). Conclusions: We devised both techniques to prove effective in achieving good valvular continence, but a significantly greater coaptation length was obtained with our track technique at the 2 years follow-up.