This paper presents experimental research on creeping discharge by using cylinder-plate electrode configurations under AC voltages. The process of creeping discharge-caused damage on the oil/pressboard insulation was studied. First, the electric field distribution was achieved by Multiphysics software simulation. Afterwards, the phenomena that occurred in the entire damage process, such as "white smoke", "white mark", and "black mark", were recorded and analyzed. Furthermore, the micromorphology of the oil-impregnated pressboard was observed via scanning electron microscope (SEM). Finally, the inner mechanism of the damage to the oil/pressboard insulation was explored according to the phenomena and the SEM morphologies. Results showed that during damage processes, the high electrical field strength (nearly 25.853 MV/m) at the weak-link point between the cylinder electrode and the pressboard directly caused the incipient discharge. The cavity, moisture, impurity, solid particle, and formation of a gaseous channel all contributed to the development of the damage. The "white smoke" consisted of gases that stemmed from the ionization of oil and evaporation of moisture. The "white mark" was the gas channel and pressboard carbonization was caused by discharge and high temperature, both of which were also the main causes of the emergence of "black mark". SEM images revealed that the pressboard successively experienced "white solid", "crack", and "pitting", which changed its surface roughness. The distorted electric field caused by gases, solid particles, and pitting further damaged the oil/pressboard. The pitting evolved into the starting point of the electrical trees and gradually led to the final breakdown.