Chiloscyphus is the largest genus of Lophocoleaceae and has ca. 250 species. In this monograph, 38 species are recognized for Australasia. Included are two new species and two new varieties. Six subgenera are recognized for Australasia: subg. Notholophocolea (R. M. Schust.) J. J. Engel & R. M. Schust., including sect. Notholophocolea J. J. Engel, sect. nov.; subg. Lophocolea (Dumort.) J. J. Engel & R. M. Schust.; subg. Connati (Lindenb.) J. J. Engel, including sect. Connati (Lindenb.) J. J. Engel, comb. nov.; subg. Microlophocolea (Spruce) J. J. Engel; subg. Septati Engel, subg. nov.; and subg. Spinoscyphus J. J. Engel, subg. nov. The largest subgenus is Lophocolea, with 20 species belonging to four sections (Lophocolea (Dumort.) J. Hentschel, Novae-zeelandii J. J. Engel, Semiteres J. J. Engel, and Aperticaules Engel, sect. nov.). Each of the species is described and illustrated. Included are two new species, C. mediinfrons J. J. Engel & Braggins, sp. nov., and C. septatus J. J. Engel, sp. nov.