Abstract: A drilling system (10) for drilling holes into concrete includes a drilling tool (20) attached to a frame (22) that can be secured to a drilling surface (S) of any orientation and permits (1) manual, (2) manual-power-assisted, or (3) stand-mounted, hands-free operation of the drilling tool (20). The system (10) utilizes air pressure, vacuum, gas regulating system, or even magnetism, to secure the frame (22) of the drilling tool (20) to the surface (S) and to control the movement of a drill bit (34) with respect to the surface (S). A fluid delivery system (80) is used to facilitate certain actions of the drill bit (34) and to effectively remove debris resulting from drilling from the drilling site. Also disclosed are related methods of drilling holes into concrete that reduce noise, mess, and debris resulting from drilling.