The genus Habenaria is one of the largest orchid genera, and although it has a broad distribution, its main centers of diversity are in Brazil, eastern Asia, and central and southern Africa. Despite its diversity, little is known about the pollinators of this genus, but the few published reports to date indicate that Habenaria sp. are mainly pollinated by moths. Here we report that the diurnal skipper Pelopidas mathias can act as a pollinator for the population of Habenaria radiata in Nara Prefecture, Japan. Previous reports have shown that another diurnal skipper, Parnara guttata, is one of the pollinators of H. radiata in Fukuoka Prefecture. The observation that two butterflies from the family Hesperiidae transfer pollinia for populations of H. radiata separated by approximately 600 km provides strong evidence that H. radiata utilizes diurnal skippers as one of its main pollinators.