Disclosed is a cooling and lubricating system (and method of use) for an RCD bearing/seal assembly comprising an internal conduit for directing fresh oil into the lower end of the bearing assembly where it can then progress upwardly through the bearing assembly and seals to provide cooling and lubrication to the internal bearings and rotary seals. The RCD system employs a small footprint oiler to deliver, via pressurized air, the oil to the RCD. Also disclosed is an RCD bearing assembly outfitted with the oil channel conduits for directing oil through the RCD bearing assembly to cool and lubricate the seals and bearings.