Similarities between the floras of geographically comparable regions of New Zealand (NZ) and the southern Andes (SA) have interested biologists for over 150 years. The present work selects vegetation types that are physiognomically similar between the two regions, compares their floristic composition, assesses the environmental factors that characterize these matching vegetation types, and determines whether phylogenetic groups of ancestral versus modern origin are represented in different proportions in their floras, in the context of their biogeographic history.Floristic relationships based on 369 genera of ten vegetation types present in both regions were investigated with correspondence analysis (CA) and ascending hierarchical clustering (AHC). The resulting ordination and classification were related to the environmental characteristics of the different vegetation types. The proportions of different phylogenetic groups between the regions (NZ, SA) were also compared, and between forest and non-forest communities.Floristic similarities between NZ and SA tend to increase from forest to non-forest vegetation, and are highest in coastal vegetation and bog. The floras of NZ and SA also differ in their phylogenetic origin, NZ being characterized by an 'excess' of genera of basal origin, especially in forests.The relatively low similarities between forests of SA and NZ are related to the former being largely of in situ South American and Gondwanan origin, whereas the latter have been mostly reconstituted though transoceanic dispersal of propagules since the Oligocene. The greater similarities among non-forest plant communities of the two regions result from varied dispersal routes, including relatively recent transoceanic dispersal for coastal vegetation, possible dispersal via a still-vegetated Antarctica especially for bog plants, and independent immigration from Northern Hemisphere sources for many genera of alpine vegetation and grassland.