Here is my quick and dirty thought. After thinking about it for a while, I may come up with a better idea?? If the instructions are a little fuzzy don't hesitate to ask for better details.
1. Attach the club head to a wooden base that can be clamped to your drill press table. I would do this by driving 3 o 4 long wood screws through the base and into the bottom of the club head. You will need to remove the weight on the bottom of the club head so you can <b>pre-drill pilot holes into the club head or you may split it.</b> After the project is complete, the weight will cover up the pilot holes so no one can see them!!
2. Find the largest drill bit that will slip into the part of the shaft that is in the head of the club and chuck it in the drill press.
3. Slip the club head/base onto the drill bit and hold it there with your third hand.[

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](Those little bungee cords with hooks on each end work wonderfully well for things like this!!)
4. With your other two hands, adjust the tilt, height and rotation of the DP table so you can clamp the base to the table with the head in the existing orientation.
5. After the base is firmly clamped, remove the drill bit from the chuck and change to one of the correct size. I would probably not try to drill the hole to final size; but rather drill it several times using successively larger bits each time. (Note: It will be easier to change out drill bits if you extend the quill and lock it in a down position when setting up the original orientation.)
If the above is a little fuzzy, my apologies; but I hope there is enough here to get you strarted in the right direction. There are most certainly other ways to accomplish your task and mine may not be the best or the easiest; but maybe it will turn a light bulb and help you solve your dilemma.