Current electric utilities must achieve reliability enhancement of considerable distribution feeders with an economical budget. Thus, optimal preventive maintenance planning is required to balance the benefits and costs of maintenance programs. In this research, the proposed method determines the time-varying failure rate of each feeder to evaluate the likelihood of future interruptions. Meanwhile, the consequences of feeder interruptions are estimated using interruption energy rates, customer-minutes of interruption, and total kVA of service areas. Then, the risk is assessed and later treated as an opportunity for mitigating the customer interruption costs by planned preventive maintenance tasks. Subsequently, cooperative game theory is exploited in the proposed method to locate a decent balance between the benefits of reliability enhancement and the costs required for preventive maintenance programs. The effectiveness of the proposed method is illustrated through case studies of large power distribution networks of 12 service regions, including 3558 medium-voltage distribution feeders. The preventive maintenance plans resulting from the proposed method present the best compromise of benefits and costs compared with the conventional approach that requires a pre-specified maintenance budget.