A pocket-hole drilling apparatus for drilling pocket-holes in a workpiece is disclosed. In one embodiment, an initiation switch actuates clamping the workpiece and the movement of a drilling module to cut a pocket-hole. The drilling module has a motor and a step-drill mounted thereon, which is slidably mounted on a guide module. The axis of the drilling module movement intersects work surface. In another embodiment, a movable fence provides the adjustability of pocket-hole depth. In yet another embodiment, two actuator tips are disposed in a fence to prevent the drilling of a pocket-hole through the sidewall of a workpiece. In still another embodiment, a short stroke clamping actuator is used to prevent human finger injury. In still another embodiment, a blower or an ejector pump is used to remove wood chips, wherein the blower is either attached to a drilling motor or to a separate blower motor; the ejector pump is mounted near the drill guide. In still another embodiment, two pocket-drills are slidably mounted on a block so as to drill two pocket-holes and to adjust pocket-hole spacing. In still another embodiment, a mounting structure is disposed either underneath or above the work surface to mount drilling module(s) so as to drill multiple pocket-holes into a wide workpiece at one setup. In still another embodiment, a drill guide forms a clearance for the cutting edges of the step-drill to minimize wear on the edges. In a further embodiment, an actuator provides both clamping and drilling movements, wherein the actuator is an electric motor or a hand lever.