Bubbles will reduce the electric strength of transformer oil, and even result in the breakdown of the insulation. This paper has studied the breakdown voltages of transformer oil and oil-impregnated pressboard under alternating current (AC) and direct current (DC) voltages. In this paper, three types of electrodes were applied: cylinder-plan electrodes, sphere-plan electrodes, and cone-plan electrodes, and the breakdown voltages were measured in both no bubbles and bubbles. The sphere-sphere electrodes were used to study the breakdown voltage of the oil-impregnated pressboard. The results showed that under the influence of bubble, the breakdown voltage of the cylinder-plan electrode dropped the most, and the breakdown voltage of the cone-plan electrode dropped the least. The bubbles motion was the key factor of the breakdown. The discharge types of the oil-impregnated pressboard were different with bubbles, and under DC, the main discharge type was flashover along the oil-impregnated pressboard, while under AC, the main discharge type was breakdown through the oil-impregnated pressboard.