
Tom M. answered 08/20/19
9 Years of Teaching and Using SketchUp
If you are using SketchUp Pro, then you can use the Solid Tools. First create a cylinder that represents where you want your hole to be. Make it into group and make sure that it is a solid. Then using the Subtract command, subtract the cylinder from your solid that has the curved surface.
Alternately, if you don't have SketchUp Pro, then the other method is more involved and uses the Intersect Faces (right mouse click) command. Cut your cylinder solid from the model and Paste it in Place inside the curved solid. Explode the cylinder and select both the cylinder and the curved surface and run Intersect Faces with Selection. Erase any unwanted geometry.