A forerunner to the
puzzle jug, fuddling cups were in production and use in the sixteenth through early eighteenth century, and were primarily an
English cultural phenomenon. Where a
puzzle jug requires the drinker to cover a set of holes or otherwise solve a
puzzle to drink, the fuddling cup merely requires extreme care not to spill. Its form is of three or four separate cups, with
handles on each side intertwining with the handle of the cup next to it. Instead of being completely separate, as they would appear upon casual analysis, the bodies of each cup are connected to each other with tubes or holes. This allows the contents to remain
stable in their separate spaces until the overall cup is tilted to a certain angle at which they can pour into the one being drunk from. At best this configuration results in an
adventurous drinking experience, and at worst the beverage of choice being spilled down the front of one's shirt.
While I couldn't find any references for this on-line, at a museum exhibit featuring a seventeenth century fuddling cup the little plaque suggested that one drinking game was to fill each cup with a different drink, shake it a little, and have the drinker try to figure out what was present. Given a suitably evil barkeep I imagine one might end up with a combination like lager, wine, and, say, milk -- more proof that the British will ingest anything, I suppose.
I also found exactly one mention of a German trick drinking cup called a Jungfernbecher, which apparently translates roughly to fuddling cup. These cups took the form of a main vessel attached to the back of a female form holding a smaller vessel, which is allowed to swivel at either side, and thus remain roughly horizontal as the cup was tipped. As part of a wedding celebration, the groom would endeavor to drain the contents of the main vessel without spilling any of those of the smaller.
As a point of interest, take a look at Webster_1913's definition of Fuddle, which is To drink to excess. This means that the word Befuddled, evidently not around in 1913 but in uncommon use today, essentially means "drunk" -- not garden-variety "confused" as would seem correct.