Chainsaws with automatic oilers use crankcase pressure to pressurize the oil tank and force oil to the chain.
I have found that when I'm finished with the saw, if I loosen the oil fill plug to allow pressure to escape, then tighten it, it reduces--does not eliminate--the amount of oil that leaks out of the saw later. Like Bert, I keep an old rag under the saw to catch what inevitably leaks out.
I prefer manual oiling but that's like trying to find a Packard car.