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Power transformer is one of the most important assets for any electricity utility. The overall power transformer health condition can be assessed through the condition of its insulation system. Furan, dissolved gas analysis, water content, breakdown voltage, interfacial tension, acidity, and oil color are commonly used as fault diagnostic oil parameters that can assess the health condition of power transformers. Degradation condition of power transformer insulation system, especially paper insulation, reflects the transformer aging condition. Unfortunately, continuous aging process of power transformer insulation system cannot be avoided due to the severe operating conditions that a transformer is operating on. So, it is very important to regularly monitor the condition of power transformer insulation to maintain its reliability. Historical data of transformer insulations are very substantial to define the history of power transformer health condition. This research introduces a method to predict the degradation condition and provide insulation index estimation of power transformers based on these historical data.