You are trying to make a hole with a hemispherical bottom. I would remove most of the material with a regular drill, them switch to the box core bit. First, of course, try it out on a piece of scrap wood of the same type as the cutting board.

If you are just making a large diameter dimple, no need to pre-drill.

Run the drill press at its maximum speed and lower the drill slowly to minimize tear out.

Any either case make sure your board is clamped in position.

You are trying to make a hole with a hemispherical bottom. I would remove most of the material with a regular drill, them switch to the box core bit. First, of course, try it out on a piece of scrap wood of the same type as the cutting board.

If you are just making a large diameter dimple, no need to pre-drill.

Run the drill press at its maximum speed and lower the drill slowly to minimize tear out.

In either case make sure your board is clamped in position.