When a pot with a drain hole rests on the ground, the soil beneath the pot serves as a wick and helps to pull water from the pot. In fact, it can be so effective it will allow growers to use grow media more water-retentive than would normally be healthy. All that's need to take advantage of the earth's wicking ability is to make sure there is a soil bridge that makes a connection between the medium in the pot and the mineral soil below the pot. From the perspective of hydrology, when you set a conventional container planting on the ground with nothing blocking the drain hole, it terns a conventional container planting into a raised bed. This fact is what gave rise to the pot in pot, pot in socket, and pot in trench techniques of growing plants (mainly nursery stock). If you open up the drain hole and use the technique, it will be pretty hard to over-water, so well does it work. Raising the pot above the ground on feet or blocks ensures that any perched water the medium supports remains in the pot; whereas, placing the pot on the ground with a connection between the pot and the ground ensures all or nearly all of the perched water will be pulled from the pot by the earth's wicking action.
Alternately, you can make a hole in whatever is blocking the drain hole and push a wick up into the medium above the drain hole.

As long as the wick is in contact with the soil below the pot, it will work as well as the soil bridge.
The best way to establish this type of set-op is by leaving the drain hole(s) wide open and sinking the pot a little into the ground, but all that's required for it to work is that bridge between the grow medium and the soil below the pot.
Al