We used 57 morphometric characters to discriminate 17 extant and fossil Cupuladria species and analyzed their phylogenetic relationships in relation to extant Discoporella species. Data were gathered from 496 extant and fossil Cupuladria specimens 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: Cupuladria with vicarious avicularia, Cupuladria without vicarious avicularia, and Discoporella. Further discriminant analyses identified 17 species of Cupuladria. 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, including Discoporella, and are consistent with previous molecular phylogenies except that there are no molecular data for the CV2 clade. Diversification of species was higher in the CV1 and CV2 clades than CNV clade, and involved mostly Caribbean species. Cupuladria with vicarious clade 1 (CV1) includes: C. monotrema, C. pacificiensis, C. exfragminis, C. cheethami, C. biporosa, and four new species: C. pervagata, C. floridensis, C. colonensis and C. dominicana. Cupuladria with vicarious clade 2 (CV2) includes: C. multesima, C. incognita, and three new species C. collyrida, C. veracruxiensis and C. planissima. Cupuladria clade without vicarious (CNV) includes: C. surinamensis, C. panamensis, and one new species C. 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 CNV appearing as the hypothetical ancestor of the two older clades CV1 and CV2. More extensive collections of early to middle Miocene specimens of Cupuladria and Discoporella will be required to resolve this apparent paradox.