Five new species of Corybas endemic to New Zealand, C. confusus, C. obscurus, C. sanctigeorgianus, C. vitreus, and C. wallii are described. These species are segregated from the Corybas trilobus aggregate based on morphometric and DNA fingerprinting (AFLP) analyses. A key to the new species is also provided, and their distribution and conservation status are included. Phylogenetic results showed that, despite the great morphological and ecological diversity of these orchids, genetic divergence between species is low, suggesting recent diversification. We also found evidence for multiple dispersal events from New Zealand to several offshore and sub-Antarctic islands.