An anti-skive drill bit including a body having a proximal end, a distal end, a longitudinal axis extending between the proximal and distal ends, and a flute extending longitudinally along the body. The distal end includes a distally facing region and a first channel defining a first channel surface. The distally facing region includes a relief surface having a first most-distal point at one of an intersection of an outer diameter of the body and a leading edge of the first flute, and an intersection of the outer diameter of the body and the first channel surface. The distally facing region has a relief surface angle between the relief surface and an outer diameter surface of the body at the first most-distal point of less than 90 degrees. The channel has a proximal end intersecting the first flute, and a distal end intersecting the relief surface.

The present drill point arrangement includes a first and second land defined by a first and second flute, with a first cutting tip and a second cutting tip formed on the first and second lands respectively. The first cutting tip being positioned a first radial distance and the second cutting tip being positioned a second radial distance, each measured from the axis of rotation. The second cutting tip is positioned next in cutting tip sequence to the first cutting tip, and the second radial distance of the second cutting tip is greater than the first radial distance of the first cutting tip. Optionally, the first cutting tip is positioned a first axial distance and the second cutting tip is positioned a second axial distance, each measured from the front tip, and the second axial distance is greater than the first axial distance.