Only one of the two shows, as expected it only shows if the ID of the quoted tweet is smaller than that of the tweet itself.
This also means that in general, you can't quote a non-existing future tweet hoping it'll be something cool in the future. Well you can but the preview won't work.
At first I thought a two-cycle would be incredibly hard. But I suppose you really only have to adjust the timestamp to forward-guess the next ID. You would know the ID of the first one. It would definitely help narrow down the algorithm used for preventing the recursion.