Abstract: A drilling apparatus and method for forming a countersunk hole into a structure. The drilling apparatus may include a drill motor housing assembly, a rotor/spindle assembly, a countersink cage, and a countersink cutter. The drill motor housing assembly may have an inlet air duct, the rotor/spindle assembly may have a first duct and the countersink cage may have a second duct. The countersink cutter may have a plurality of flutes formed into a cutting end thereof. The countersink cutter may also have a third duct formed therethrough and a plurality of exit ducts common with the flutes. Each duct of the drilling apparatus may be fluidly coupled such that inlet air may be forced through the inlet air duct, through the first duct, through the second duct, through the third duct, and then through the plurality of exit ducts during drilling via the drilling apparatus.