Recent studies of Solanum L. (Solanaceae) phylogeny using both plastid and nuclear DNA sequences have shown that a distinct clade comprising the members of Solanum sect. Geminata (G. Don) Walp. (woody, non-spiny solanums with simple or branched trichomes and usually leaf-opposed inflorescences) also includes a small Caribbean group of species known as section Diamonon (Raf.) A. Child, whose relationships have previously been obscure: S. acropterum Griseb., S. conocarpum Dunal, S. havanense Jacq., and S. troyanum Urb. Work on a monograph of section Holophylla (G. Don) Walp. (s.l.) has also revealed that several species previously excluded from section Geminata on morphological grounds belong to the more broadly circumscribed group recognized as the Geminata clade. In addition, since the publication of the monograph of Solanum sect. Geminata, seven new species of these rare, forest understory shrubs have been described (S. chalmersii S. Knapp, S. humboldtianum Granados-Tochoy & S. Knapp, S. monanthemon S. Knapp, S. naucinum S. Knapp, S. pseudodaphnopsis L. A. Mentz & Stehmann, S. sagittantherum Granados-Tochoy & C. I. Orozco, and S. sumacaspi S. Knapp). An additional new species from Ecuador, S. elvasioides S. Knapp, is described here. I review the status and circumscription of section Geminata in the New World and its relation to the Geminata clade, and provide descriptions for all the species of the Caribbean S. havanense species group and all species previously excluded from section Geminata. Lectotypes are selected for S. acropterum, S. hookerianum A. Spreng., S. myrtifolium Lodd., S. havanense Vell., S. troyanum, S. argentinum Bitter & Lillo, and S. evonymoides Sendtn., and a neotype is selected for S. havanense.