A fastener installation tool including a guide that guides a fastener into a side of a work piece at an angle, while optionally restraining the fastener from wobbling due to rotation, even upon initial entry into the work piece. The guide can define an angled bore including a fastener entrance opening and a fastener exit opening which is adapted to be positioned immediately adjacent the work piece. The guide can include a material ejection port between the openings, through which material bored from the work piece can be evacuated from the angled bore to prevent binding of the material with the fastener. The tool can include a clamp assembly that clamps opposing sides of the work piece to precisely align and steadily hold the angled bore as a fastener is being installed in a side surface. Related methods of using the tool to install fasteners also are provided.