The withstand voltage performance of the metallized film is the key factor determining the reliability of the capacitor. This study investigates the influence of electrode contact configuration on the dielectric breakdown characteristics of metallized biaxially oriented polypropylene (BOPP) films. Experiments are conducted using two distinct setups: one with the film’s metal layer contacting a high-voltage electrode and the other with it contacting a ground electrode. The results demonstrate a significant configuration-dependent effect. When the metal layer contacts the high-voltage electrode, the film exhibits a lower average breakdown strength of approximately 386.7 V/μm, accompanied by pronounced self-healing discharges and electrode clearing. In contrast, contact with the ground electrode yields a higher average breakdown strength of ~517.1 V/μm without observable self-healing, leading to a smaller breakdown area. Weibull analysis further indicates that the former configuration has a lower characteristic breakdown strength but higher data reliability. The disparity is attributed to a higher concentration of shallow traps and insulation weak points at the BOPP/metal interface under high-voltage contact, which facilitate charge injection and promote breakdown. These findings provide critical insights for optimizing the insulation design and electrode configuration of metallized film capacitors in high-voltage applications.