The Schottky injection barrier plays a crucial role in determining the charge movement and migration process, yet its electric field and temperature properties remain unclear. The precise determination of the Schottky injection barrier value is essential for understanding the charge migration dynamics at the interface between the metal electrode and the oil-pressboard insulating medium. This study introduces a computational approach to determine the Schottky injection barrier, derived from classical Schottky emission theory. The methodology employed in this research aligns with previous studies, utilizing the Schottky emission current mechanism to describe steady-state conduction current. Results indicate that the Schottky injection barrier increases with temperature, with a 17.09% rise for oil-electrode and an 8.3% increase for pressboard-electrode in the temperature range of 299 K to 353 K. These temperature-dependent variations are attributed to the negative temperature dependence of the Fermi energy levels of the metal electrodes. Furthermore, the impact of electric field strength on the Schottky injection barrier is found to be minimal. By developing a bipolar charge transport simulation model and validating the injection barrier for 0.5 mm oil-immersed pressboard, this study confirms the accuracy of the calculated Schottky injection barrier. The insights provided in this research could aid in simulating charge transport and analyzing charge characteristics in oil-paper/pressboard insulation systems.