A lubrication system for a rack and pinion mast of a drilling rig includes a lubricating pinion positioned on a cart and in engagement with the rack. The lubricating pinion includes a plurality of lubrication dispensing ports formed on faces of the teeth of the pinion. The lubrication dispensing ports are fluidly coupled to lubrication ports formed in the lubricating pinion. The lubrication ports fluidly couple to an inner bore of the lubricating pinion. The inner bore may be fluidly coupled to a lubricant reservoir.