From Wikipedia:

"A Pythagorean cup looks like a normal drinking cup, except that the bowl has a central column in it, giving it a shape like a Bundt pan. The central column of the bowl is positioned directly over the stem of the cup and over a hole at the bottom of the stem. A small open pipe runs from this hole almost to the top of the central column, where there is an open chamber. The chamber is connected by a second pipe to the bottom of the central column, where a hole in the column exposes the pipe to (the contents of) the bowl of the cup."

I printed this with TPU and no supports. It came out pretty well.