A cylinder lubrication system comprises a cylinder liner defining a cylinder, a piston reciprocally mounted in the cylinder for axial travel along a cylinder axis and having a piston skirt that moves in close proximity with the cylinder, an oil supply passage extending substantially circumferentially about an outer surface of the cylinder liner, an oil supply line fluidly connecting the oil supply passage to an oil supply, a series of small holes extending radially through the cylinder liner, from the cylinder to the oil supply passage, and operable as oil passages for lubricating oil from the oil supply to flow to the upper portion of the cylinder.