Ten fairly well-preserved enameled glass fragments were recovered from the summit of Masada during the 1963-1965 excavations. They are dated 20 to 70 CE based on the shape of the vessel and the accepted date for this technique in the first century. These fragments were found in contexts that have been disturbed by first- to seventh-century residents on the site; their original owners can only be hypothesized. A catalogue of these fragments, comprising eight to ten different cups, describes each fragment in detail and analyzes its subject and painting technique. The gladiator, charioteers and horse, and the bird as a base mark are unique to Masada. The garland, vines, and base dots are similar, even identical, to images on published enameled glass cups of this period from Europe. The origin of these cups, as that of all contemporaneous enameled cups, remains a mystery. The festival of the Floralia is suggested as a unifying iconographic theme.