A cylinder cooling apparatus for an air-cooled engine is equipped with a cooling fan provided on one end section of a crankshaft; a pair of pushrod insertion holes for air intake and exhaust valves formed in a cylinder outer circumferential wall section; a fan shroud for covering the cooling fan and for covering the cylinder outer circumferential wall section in which the pushrod insertion holes are formed; a cutout ventilating section formed in the cylinder outer circumferential wall section between the pair of pushrod insertion holes; and tunnel-shaped ventilating holes formed in the cylinder outer circumferential wall section between the pushrod insertion hole disposed on the side of the cooling fan and a cylinder bore and extending from the cylinder outer circumferential wall section on the side of the cooling fan to the cutout ventilating section.