We used 57 morphometric characters to discriminate 17 extant and fossilCupuladriaspecies and analyzed their phylogenetic relationships in relation to extantDiscoporellaspecies. Data were gathered from 496 extant and fossilCupuladriaspecimens ranging in age from early Miocene to Recent and distributed from the Caribbean to tropical eastern Pacific. A first series of discriminant analyses distinguished three morphological groups:Cupuladriawith vicarious avicularia,Cupuladriawithout vicarious avicularia, andDiscoporella. Further discriminant analyses identified 17 species ofCupuladria. Cladistic analyses of these three groups yielded four equally parsimonious trees. All of the consensus trees exhibited the same topology, dividing the 25 tropical American cupuladriids into four distinct monophyletic clades, includingDiscoporella, and are consistent with previous molecular phylogenies except that there are no molecular data for the CV2clade. Diversification of species was higher in the CV1and CV2clades than CNVclade, and involved mostly Caribbean species.Cupuladriawith vicarious clade 1 (CV1) includes:C. monotrema,C. pacificiensis,C. exfragminis,C. cheethami,C. biporosa, and four new species:C. pervagata,C. floridensis,C. colonensisandC. dominicana.Cupuladriawith vicarious clade 2 (CV2) includes:C. multesima,C. incognita, and three new speciesC. collyrida,C. veracruxiensisandC. planissima.Cupuladriaclade without vicarious (CNV) includes:C. surinamensis,C. panamensis, and one new speciesC. gigas. The stratigraphic occurrence of species is consistent with cladogram topology within clades. However hypothesized cladistic relations among clades are the reverse of their stratigraphic occurrence with younger clade CNVappearing as the hypothetical ancestor of the two older clades CV1and CV2. More extensive collections of early to middle Miocene specimens ofCupuladriaandDiscoporellawill be required to resolve this apparent paradox.