Phylogenetic analyses of nuclear DNA external transcribed spacer (ETS) and chloroplast DNA trnL–trnF markers were undertaken to reconstruct the evolutionary history of the South Pacific genus Melicytus. Bayesian analyses of the ETS sequence data produced a phylogenetic tree with several well supported groups, including clades comprising: (1) species from Australia, Tasmania and Lord Howe Island; (2) the Norfolk Island M. latifolius and New Zealand off-shore island M. novae-zelandiae subsp. novae-zelandiae; (3) the large-leaved M. ramiflorus complex; (4) M. fasciger and M. micranthus; and (5) M. obovatus and allies from the Cook Strait region. Phylogenetic analysis of trnL–trnF sequence data also retrieved some of these groups although, in general, was not as well resolved. The relationships of M. lanceolatus are equivocal, as in the ETS phylogeny it is sister to a clade comprising the large-leaved tree species M. fasciger and M. ramiflorus complex and the small-leaved M. micranthus, whereas in the trnL–trnF phylogeny it is sister to a clade of small-leaved shrub species such as M. alpinus and M. crassifolius. Several biogeographic patterns are evident, with dispersal to the west from New Zealand, to Australia, involving small-leaved shrub species. Dispersal to the north from New Zealand, to Norfolk Island and Fiji, involves large-leaved tree species. The sex expression is documented for all named species and undescribed entities, with these being either hermaphroditic or dioecious. When sex expression is mapped onto the phylogeny, the hermaphroditic system is inferred to have evolved from the dioecious system. New chromosome counts are presented for M. angustifolius (2n = 64) and M. dentatus (2n = 32), and earlier counts of 2n = 64 are confirmed for M. crassifolius and M. alpinus. An additional 17 counts are provided for two natural hybrids and several undescribed entities from Australia and New Zealand. The polyploid chromosome number of 2n = 64 occurs most frequently in small-leaved divariate plants with hermaphroditic flowers. When chromosome numbers are plotted onto the phylogeny it is inferred that high polyploids (e.g. 2n = 64) and small-leaved shrubs have evolved from large-leaved trees with functional diploid (e.g. 2n = 32) chromosome numbers.