Dwarf elephants are quite well known from the western Mediterranean islands, but they are still poorly documented in most eastern Mediterranean islands. This paper reports on the discovery of a third lower molar of a dwarf elephant from the island of Kassos, which is situated in the southern Aegean, between Crete and Karpathos. This molar is determined as Palaeoloxodon aff. creutzburgi, a dwarfed species known from the Late Pleistocene caves and deposits in Crete and derived from the mainland straight-tusked elephant P. antiquus. An upper molar (M3) from the island of Dilos, previously referred to Elephas antiquus or E. mnaidriensis, is also redescribed. It is almost identical to the upper molars of a paleoloxodontine elephant from Naxos. Its small size and lack of sufficient comparative material lead us to determine it as Palaeoloxodon sp. The palaeogeographic evolution of the Aegean region during the Pleistocene and its impact on the dispersal of elephants in the Aegean islands are discussed.