Syllid annelids from the so-called ‘ribbon clade’ are flattened, ribbon-shaped worms of the genera Parahaplosyllis Hartmann-Schröder, 1990, Eurysyllis Ehlers, 1864, Xenosyllis Marion & Bobretzky, 1875, Trypanosyllis Claparède, 1864, Ramisyllis Glasby, Schroeder & Aguado, 2012, Trypanobia Imajima & Hartman, 1964, Plakosyllis Hartmann-Schröder, 1956, Pseudosyllis Grube, 1863 and Trypanedenta Imajima & Hartman, 1964. Some species possess a remarkable reproductive strategy using multiple stolons that has been recently suggested to be ancestral to the group. Here, to evaluate the evolution of reproductive modes in the group, we assess, for the first time, the phylogenetic relationships within the ribbon clade and related genera. We collected new material of Trypanobia and Trypanosyllis from Japan, Spain, Philippines and Indonesia and sequenced it for the nuclear markers 18S rRNA and the mitochondrial markers 16S rRNA and cytochrome c oxidase I for phylogenetic inference and also performed ancestral character reconstruction for the reproductive strategy in the entire group. Formal taxonomic descriptions of a new genus and six new species are provided. The new genus, Trypanospina, gen. nov., is characterised by the spines that cover its surface. Most genera within the ‘ribbon clade’ are monophyletic and the relationships appeared well supported in most cases. However, our phylogenetic hypotheses are not conclusive in regard to the relationships of the genera Trypanedenta and Trypanobia, nor to the status of those to genera as distinctive, since they seem to be paraphyletic and they appear in low-supported clades. In contrast, our results shed light on the evolution of the reproductive modes within the group, showing that scissiparity (development of a single stolon each time) is the ancestral character for the entire group and gemmiparity (development of more than one stolon at the same time) then appeared twice in two independent clades.