The pike-characin Oligosarcus is a group of Characidae composed of 22 species, which have mostly allopatric distributed species in southeastern South America and sympatric occurrence of few species. Oligosarcus shares a similar distribution pattern with other fish genera and therefore, can help us to understand biogeographic events that influenced freshwater fish distribution in the southeastern South America. Our paper presents the most extensive taxonomic coverage for molecular analysis of Oligosarcus and uses various methods to examine the evolutionary history of the genus. Phylogenetic relationships among species of Oligosarcus were examined using a multilocus dataset by Maximum Likelihood and Bayesian methods. A relaxed molecular clock was used to estimate lineage divergence times, which provide a framework to examine the biogeographic history of this clade across the drainage basins of southeastern South America. Oligosarcus was resolved as monophyletic with strong support, and related to lineages currently assigned to the genus Astyanax. Within Oligosarcus, two groups of approximately equal species richness were resolved as monophyletic, mainly restricted to continental and coastal drainages of southeastern South America. Oligosarcus radiation is estimated to the late Neogene, with its origin in the Pliocene and most speciation events occurring in the Pleistocene. Some apomorphic characteristics associated with piscivory (e.g. large caniniform teeth) in Oligosarcus likely have evolved once, and are convergent to similar phenotypes observed in a distantly related clade of Astyanax (formerly Bramocharax). In addition, the presence of morphological convergence within the genus Oligosarcus (e.g. trophic morphology) seems to explain the difference between the present molecular hypothesis and some previous morphological studies. Ancestral geographical range estimation using analytical methods (e.g. DIVALIKE and DEC) demonstrated the effects of different Landscape Evolution Models (LEMs) on diversification of Oligosarcus. The results suggest that the two main Oligosarcus clades evolved in allopatry in continental and coastal drainages, with subsequent range extension and vicariance events that established the modern distributions. LEM analyses indicate the importance of formation of riverine barriers across the watershed of the La Plata basin and the effects of sea-level changes during the Pleistocene for delineating lineage distributions of Oligosarcus.