A pilot pin assembly is slidably receivable within a tool bit of a drill press. The pilot pin assembly includes a first pin defining an interior cavity, and a second pin at least partially received within the interior cavity of the first pin. A spring is positioned within the interior cavity for biasing the second pin toward an extended position relative to the first pin.

A holesaw assembly includes a holesaw and a pilot bit. The holesaw includes a hollow cup defining a center axis. The cup has a round base perpendicular to the center axis and a peripheral wall coupled to and extending axially forward of the base to a peripheral edge at a free end of the wall. The pilot bit is received in the holesaw along the center axis. The pilot bit has a shaft received in the base, a cutting head coupled to a front end of the shaft, and an at least partially threaded tip coupled to a front end of the cutting head. The holesaw is free of any radial cutting elements disposed inside the cup between the drill bit and the peripheral wall of the cup.