Oil–air lubrication has proven to be very effective for high-speed bearings because the oil supply in the form of droplets can be precisely controlled. This work uses optical interferometry to study the mechanism of lubricating film formation in rolling point contact with oil droplet lubrication. The effect of a double oil drop pair, where two oil droplets are positioned in mirror images about the central axis of the lubricated track, is examined. The process by which pairs of oil droplets approach and lubricate a bearing contact is analysed. This study also covers the effect of multiple oil droplets supplied in a tailored or a random dispersion pattern. Additionally, the effects of oil viscosity, entrainment velocity, and droplet distribution on starvation are also investigated.