To fit up the wooden handle, first lay out the tang on the block and scribe the outline.
Next align the block in the drill press so that the drill will follow the line of the tang.
Drill out as much of the material as you can. If you reverse the handle you and follow the scribed lines your holes will meet accurately. You can remove the webbing if any with the drill freehand, but be careful not to cut beyond the scribe lines.
Next cut out the remaining webbing and open the hole, try fitting the tang as you go, until you have a nice tight fit and the handle seats itself against the guard squarely. In this photo, I am using a hole saw to rip out the hole. It is a very handy tool and will cut most handle materials quickly. I also use a four square rasp for the final fit.