The influence of carrier mobility on the space charge transport behavior inside the oil-impregnated pressboard insulation of converter transformers cannot be neglected. However, at present, current knowledge is usually derived from empirical or theoretical values, lacks experimental studies, and often ignores the effects of temperature and field strength under actual operating conditions. In this paper, based on the variable-temperature surface potential decay (SPD) method, a carrier mobility measurement platform for oil-impregnated pressboard is established, and the carrier mobility values for different combinations of oil and oil-impregnated pressboard are obtained experimentally to analyze and reveal the influence mechanisms of temperature and field strength on the carrier mobility. The results indicate the following: (1) The positive and negative carrier mobilities of oil-impregnated pressboard are in the range of 10−12–10−13 m2·V−1·s−1, and the negative carrier mobility is always higher than the positive carrier mobility. (2) The carrier mobility is positively correlated with the changes of temperature and field strength, and when the temperature increases from 20 °C to 80 °C, the positive and negative carrier mobilities increase by 4.01 times and 4.72 times, respectively; when the field strength increases from 1 kV/mm to 7 kV/mm, the positive and negative carrier mobility increases by 2.53 and 2.72 times, respectively. (3) The carrier mobility of the pressboard with a higher oil absorption rate changes more significantly with temperature; when the field strength is 7 kV/mm and the temperature increases from 20 °C to 80 °C, the positive polarity carrier mobility increases from 3.96 × 10−13 m2·V−1·s−1 to 2.64 × 10−11 m2·V−1·s−1, an increase of 66.67 times, while the increase in the carrier mobility of the pressboard with a lower oil absorption rate is only 1.59 times. (4) The carrier mobility of the naphthenic transformer oil-impregnated pressboard is higher than that of the paraffin-based transformer oil-impregnated pressboard, and the carrier mobility of two kinds of naphthenic transformer oil-impregnated pressboard is 3.16 times and 2.47 times higher than that of the paraffin-based transformer oil-impregnated pressboard, respectively, under the conditions of 60 °C and 7 kV/mm. (5) Utilizing the Darcy model and microscopic scanning results of the pressboard morphology, it was revealed that permeability and fiber structure are key factors influencing the variation in carrier mobility. The research results of this paper can provide theoretical basis for the calibration and optimization of the oil-pressboard insulation structure of converter transformers.