O. fleischmannii was first described from Lassithi, Crete by Hayek in 1925 and is named in honour of Herr H. Fleischmann, an Austrian headmaster and botanist.

This species is a member of the O. omegaifera group with a distribution that's not yet fully understood but which certainly encompasses the Aegean basin, Crete and some of the Cycladic islands. It is not at all a common orchid anywhere in its range and is frequently to be found growing in close association with its more widespread cousin O. omegaifera. Hybridization is well known and the resulting intermediates can be the source of considerable confusion with identification.

In its genetically pure form, O. fleischmannii is however easily distinguished from O. omegaifera by its significantly smaller size and importantly the dense silver hair that covers the lower median and lateral lobes. The speculum is tipped with a white omega and always shiny but colour may vary from slate grey to an improbably vivid red. Lateral lobes are small and usually not folded back as tightly as in O. omegaifera.

Its habitat preference is invariably based on calcareous substrates but may be in a full sun position in rocky garrigue or the semi shade of open pinewoods. It also seems to be happiest growing at altitude and in Crete the mountains around Thripti and Oreino are good locations to seek it out. It flowers from February until April and unusually for this group can produce up to eight individual flowers alternately up a stem that can reach to more than 20cms. The illustrations are from eastern Crete, dating from the first week of April.