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The electrical insulation structure of most power transformers is a combination of insulating oil and solid materials. One of the crucial problems we face in transformer operation is flow electrification, which occurs at a flowing oil/solid material interface. Thus, for the transformer insulation design, we need to clarify the now electrification phenomena. In this paper, we measured the electric field strength in an oil/pressboard composite insulation system using an electro-optic method of the Kerr effect. We obtained the time variation of electric field distribution in both flowing uncharged and charged oil. It is notable that we could quantitatively clarify the electric field distortion in flowing charged oil by flow electrification. Furthermore, we measured the leakage current from divided electrodes and derived a charge density distribution along the flow direction. Finally, we quantitatively discussed the electric field distribution and the charge behavior from the measurement results.