This article presents an optimization methodology to schedule the replacement of power transformers (PT) into a fleet. The objective is the minimization of the summation of the risk indices of the PT. Each PT risk index is calculated from the estimation of the life used and the strategic importance of the unit. The PT life used is estimated as a relationship of the solid insulation polymerization degree, where aging processes due to oxidation, hydrolysis, and pyrolysis are considered from the calendar date when the unit starts its operation until different future scenarios. For the calculation of the PT strategic importance, financial, security, environmental, and network performance aspects are considered. Then, using the optimization model, together with the CAPEX and the available budget over a planning time, a strategy for optimally replacing the critical units is determined. The model was applied for a group of 102 units, demonstrating its applicability and effectiveness. The developed methodology serves to support the manager of these assets in making decisions in the long term.