Venation architectures and cuticular micromorphology of leaf fossils play important roles in higher-level taxonomic segregation, as these characters are broadly fixed within major plant clades. Three common fossil plant taxa are characterized by similar-shaped leaves or leaflets and anastomosing venation to such an extent that examples have commonly been assigned to the wrong taxon in past studies where fragmentary or ill-preserved material is available. We use standardized descriptions of vein cross-connection types and stomatal features to compare and contrast the venation patterns and stomatal architectures of these genera. Our reanalysis of the macro- and micromorphology of Glossopteris, Sagenopteris and Anthrophyopsis leaves reveals important differences that help segregate these taxa even on the basis of incomplete specimens. Anthrophyopsis has distinctive alignments of vein cross-connections in the outer lamina and paracytic stomata consistent with those of Bennettitales. Glossopteris has perigenous and monocyclic—normally stephanocytic to actinocytic—stomata commonly protected in pits or by overarching papillae. Sagenopteris has more consistently evanescent midribs and surficial anomocytic or stephanocytic stomata with weakly modified subsidiary cells. Considering the putatively close relationship of glossopterids (Glossopteris), Caytoniales (Sagenopteris) and Bennettitales (here encompassing Anthrophyopsis) resolved as members of the ‘glossophyte’ clade in some past phylogenetic studies, cuticular features suggest that these groups are not closely related. In addition, anastomosing venation, superficially similar to that of Glossopteris, Sagenopteris and Anthrophyopsis appears to have arisen independently in numerous other plant groups suggesting that this character has ecological or physiological benefits and is strongly prone to homoplasy.