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What size hole to drill?

Standard Fender Pickguard Screws should be a 5 x 7/16 and the recommended hole size for that would be 3/32, however I would experiment with your screw in a similar material. If wood is softer, you may want to do a 1/16 hole - I have. The screw can compress the wood and give you a tighter fit. When I use a 1/16 drill I will create a slight shallow chamfer with the 3/32 to clear a way so the paint doesn't chip. Either way you need to get in and out straight.