Subgeneric diagnoses are given for all stages of the subgenus Uresipedilum. Sasa et Kikuchi, 1995 of Polypedilum Kieffer, 1912. A key to the male imagines of the Afrotropical members of the subgenus is given. A phylogenetic analysis based on all available material of Uresipedilum from all zoogeographical regions is presented. The subgenus can be divided into three distinct groups, with additional species of uncertain placement. The annulatum group consists of five Afrotropical species with two Nearctic species as their sister group. The convictum group shows East Asian - Nearctic vicariance with four Japanese, one Nearctic and Japanese, one Nearctic and one Palaearctic and Oriental species. The oresitrophum group shows a multiple sister group relationship within a Gondwanian lineage with three Afrotropical species, three species from New Zealand, and one species from Australia. Ten new Afrotropical species are described: P. (U.) dossenudum sp. n. as male imago, pupa and larva; P. (U.) plautum sp. n. and P. (U.) lehmanni sp. n. as male imagines and pupae ; and P. (U.) spinibojum sp. n., P. (U.) praegnans sp. n., P. (U.) harrisoni sp. n., P. (U.) freemani sp. n., P. (U.) acutulum sp. n., P. (U.) kakumense sp. n., and P. (U.) gladysae sp. n. as male imagines only. P. (U.) annulatum Freeman, P. (U.) kibatiense Goetghebuer and the European P. (U.) convictum Walker are redescribed as male imagines. Two species, P. (P.) ephippium Freeman and P. (P.) anderseni sp. n. belonging to the nominal subgenus Polypedilum are described or redescribed.