This page shows how to drill a crankshaft for pressure oiling.  This was a period modification to the Model T engine. The diagram below is from a 1925 article by Murray Fahnestock

Unlike this diagram, we prefer to drill the webs all the way through, since this makes it easier to align the holes when drilling from the journals to the web. The photo below, shows Fred Houston with our homemade fixture for holding the crankshaft.  

More recently the fixture has been mounted on unistrut to make it easier to slide it around on the drill press table. We use 3/16 inch aircraft extension bits which are 6 inches long.  A spare drill or a 3/16 inch rod can be used to make sure the holes are aligned

When drilling from the journals to the webs, start in the horizontal position, then tilt the drill press table after the hole is started.  Use plenty of oil and clean the hole frequently.  Be very careful when the drill approaches the intersecting hole, since the bit can break easily when it first breaks through.