The migration and distribution of lubricant oil in a rolling bearing strongly affect the elastohydrodynamic lubrication performance between the balls and rings. However, oil re-lubrication is highly dependent on the bearing design, which is different from the ball-on-disc model. This study directly observed the distribution of the lubricant film in a custom-made model-bearing rig, with an outer ring replaced by a glass ring to allow full optical access. The influence of the cage type and surface properties were presented. The physical origin of the re-lubrication mechanism, including capillary flow and mechanical redistribution, was discussed.