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To ensure long-term reliability of transformers, it is important to identify the degradation characteristics of insulating oil in long-term operations, which are the dominant factors of the transformer dielectric strengths. Analysis on aged field insulating oil was conducted to identify how insulating oil in transformers changes and deteriorates with increasing age and what are the impacts on the electrical characteristics such as breakdown voltages. Insulating oil samples were collected from a total of 98 transformers, varying significantly with six manufacturers, manufacture years of 1956 to 1999, and voltage classes of 66 kV to 500 kV. Electrical, physical and chemical characteristics were obtained, and the impact of increasing age and the relationships among characteristics were evaluated. The characteristics found to deteriorate with increasing age were volume resistivities, dielectric loss tangents, interfacial tensions, and total acid values. These characteristics can be used as effective indexes for trend monitoring to identify aging statuses and detect abnormalities at an early stage. The physical characteristics (kinetic viscosities, densities, and flash points) showed different tendencies depending on the oil type and age. Since the physical characteristics depend on the compositions of insulating oil, the possible causes for this result are that the compositions of insulating oil were different between oil types and that the compositions varied in accordance with increasing age. Furthermore, the correlations between characteristics were evaluated. As a result, a correlation was found between volume resistivities and total acid values, and good correlations were found between interfacial tensions and volume resistivities and total acid values. Interfacial tensions, which change with a higher rate than total acid values, can be possibly used as an effective index for insulating oil degradation.