A pocket-cutting/screw-insertion system is configured for cutting screw pockets in a work piece and inserting screws therein. The system includes a clamp assembly, a router assembly, a drill assembly, and a delivery/insertion assembly including a screw delivery tube for delivering a screw, a stop block for arresting forward motion of the screw, an insertion rod for pushing the screw into the screw pocket and screw bore, and a screw channel for supporting the screw as it is inserted into the screw pocket and screw bore, wherein the stop block is positioned above the insertion rod and the screw channel such the screw first falls from the stop block onto the insertion rod once the stop block arrests forward motion of the screw and then falls from the insertion rod onto the screw channel. A method of using the system is also disclosed.