Little is known about the specific origins of the stirrup cup, but it seems clear that they are tied in with the advent of mounted packs hunting exclusively fox. The custom is essentially English, though old cups have been manufactured both in America and Germany as well. As hunting men gathered on horseback a welcome drink was a typical start to the day.

Between 1670 and 1760 "dram cups" or "tot cups" were used to serve drinks to riders. These small two-inch silver handled bowls with feet have been referred to as stirrup cups. It is generally accepted, however, that the distinction between these predecessors and the classic form is that stirrup cups are a shape easily held in the hand while on horseback, and therefore had no need of a foot.

The classic mask or head stirrup cups date from 1760. Early examples of fox and hound heads were hand-chased silver made in two halves and soldered together. Typically in this type of art, silver is soon followed by earthenware. English examples of porcelain stirrup cups date back to 1770. Inscriptions are often found around the rims of the cups.

Still available today, stirrup cups have been popular for over 200 years and have been manufactured in many forms by many companies.