Self-healing (SH) in metallized polypropylene film capacitors (MPPFCs) can lead to irreversible damage to electrode and dielectric structures, resulting in capacitance loss and significant stability degradation, especially under cumulative SH conditions. To enhance the reliability assessment of MPPFCs post-SH, this study conducted SH experiments on MPPFCs, examined the damage patterns of the electrodes and dielectric films, and proposed a novel capacitance evaluation method for MPPFCs under cumulative SH conditions. The results reveal that with increasing SH voltage, the number of dielectric layers experiencing single SH breakdowns rises, SH energy significantly escalates, and the loss area of the electrode due to high-temperature evaporation expands. Under cumulative SH conditions, the number of SH events is linearly correlated with the total number of SH-breakdown film layers and shows an exponential decay with the average single SH energy. By utilizing a Support Vector Machine (SVM) to classify the SH condition and damage features within the capacitor based on the correlation and distribution patterns of SH feature parameters, this study introduces an advanced method for evaluating the capacitance of MPPFCs under cumulative SH conditions. This method promises to improve the predictive maintenance and reliability of power electronic systems utilizing MPPFCs.