The power transformer is an important part of the power grid. The aging of oil-paper insulation is affected by many factors such as temperature and moisture. In order to accurately evaluate the service life of transformer and ensure the stable operation in power system, a method for predicting the lifetime of oil-immersed pressboard under different temperatures and moisture content was proposed. This method is mainly realized by the chemical reaction kinetic equations and transformation factor. Firstly, the effect of temperature and moisture content on the frequency dielectric response of oil-paper insulation was studied by frequency domain dielectric spectroscopy method. The results show that the dielectric loss of oil-immersed pressboard increases with the increase of moisture content and temperature. The activation energy of oil-immersed pressboard also increases exponentially with the increase of moisture content. Then, we analyzed the trend of polymerization degree of insulation pressboard in aging process and calculated the insulation life and the remain lifetime by combining the cellulose degradation kinetic models and translation factor. When the moisture content of the oil-immersed at 70 °C, the life expectancy of oil-paper insulation is about 19.26 years.