Although I'm not really full bottle on piston engines, hopefully this gas turbine engine oil system schematic can partially answer your question. In a gas turbine engine air is bled from the compressor to pressurise engine seals, so you can draw similarities between the two.
As you can see, the oil is scavenged from the gearbox and power section sumps by two separate pumps where it proceeds through two separate air/oil separators. After passing through scavenge filters and coolers, it returns to the oil tank (bottom left of image up to top right of image. The air, however, is routed from the separators up to the oil tank. These lines can been seen up through the centre of the image.
At the top of the image is an oil tank pressurising valve. This valve maintains 8.5 PSIG in the tank, the rest is dumped via the pressurising valve. After being dumped, it is routed through the power section gearbox. At this point, the air still contains some oil. By routing it through the gearbox before it is vented overboard (in to the turbine exhaust, bottom right of image), oil loss is minimised.