Background: Surgical management of an anterior leaflet prolapse remains comparatively challenging and has led to the lack of any firmly established standard repair techniques, as seen in cases of posterior leaflet prolapse. Chordal transposition repair is widely acknowledged as a remarkably durable technique that utilizes the patient’s native chordae. This study aims to evaluate and predict the biomechanical and functional characteristics of a normal mitral valve (MV) model and a pathological MV model featuring anterior ruptured mitral chordae tendineae (RMCT), and to assess the effectiveness of the chordal transposition repair in the pathological MV model. Methods: There are four stages in the proposed virtual MV repair evaluation protocol: (1) modeling the virtual pathological MV model with an anterior (A2) RMCT; (2) performing chordal transposition as the virtual MV repair procedure; (3) dynamic finite element simulation of the normal (control) MV model, the pre-repair (pathological) MV model, and the post-repair (chorda transposition) MV model; (4) assessment and comparison of the physiological and biomechanical features among the normal, pre-repair, and post-repair cases. Results: The pathological MV model with anterior RMCT clearly demonstrated a substantial flail, a marked increase in chordal stresses on the two intact chordae adjacent to the ruptured A2 chordae, and severe anterior leaflet prolapse due to the A2 chordal rupture. The virtual chordal transposition demonstrated remarkable efficacy in mitigating the stress concentrations in the leaflet and chordae, restoring leaflet coaptation, and resolving anterior leaflet prolapse. Conclusions: This virtual MV surgery strategy offers a valuable means to predict, evaluate, and quantify functional and biomechanical improvements before and after MV repair, thereby empowering informed decision-making in the planning of chordal transposition interventions.