Correns ' s 1903 ( Berichte der Deutschen Botanischen Gesellschaft 21: 133 -147) crosses between a monoecious and a dioecious species of Bryonia revealed the simple Mendelian inheritance of dioecy and provided the fi rst instance of an XY sex determination system in any organism. Bryonia ranges from the Canary Islands to Central Asia and comprises seven dioecious and three monoecious species; its closest relative, Ecballium elaterium , has dioecious and monoecious populations. We used chloroplast (cp) and nuclear (nr) gene phylogenies to infer sexual system evolution in Bryonia . We also tested for associations between sexual system and ploidy level, based on published and original chromosome counts. Confl icts between cp and nr topologies imply that the dioecious hexaploid B. cretica arose from hybridization(s), probably involving the dioecious diploids B. dioica , B. syriaca , and/or B. multifl ora . A tetraploid dioecious endemic on Corsica and Sardinia probably originated from B. dioica via autopolyploidy. While the cp phylogeny resolves few species relationships, the nr tree implies at least two evolutionary changes in sexual system. There is no correlation between sexual system and ploidy level. Molecular clocks suggest that the deepest divergence, between a species on the Canary Islands and the ancestor of all remaining species, occurred ca. 10 million years ago.