Fossil Diodontidae in Tropical America consist mostly of isolated and fused beak-like jawbones, and tooth plate batteries. These durophagous fishes are powerful shell-crushing predators on shallow water invertebrate faunas from Neogene tropical carbonate bottom, rocky reefs and surrounding flats. We use an ontogenetic series of high-resolution micro CT of fossil and extant species to recognize external and internal morphologic characters of jaws and tooth plate batteries. We compare similar sizes of jaws and/or tooth-plates from both extant and extinct species. Here, we describe three new fossil species including †Chilomycterus exspectatus n. sp. and †Chilomycterus tyleri n. sp. from the late Miocene Gatun Formation in Panama, and †Diodon serratus n. sp. from the middle Miocene Socorro Formation in Venezuela. Fossil Diodontidae review included specimens from the Neogene Basins of the Proto-Caribbean (Brazil: Pirabas Formation; Colombia: Jimol Formation, Panama: Gatun and Tuira formations; Venezuela: Socorro and Cantaure formations). Diodon is present in both the Atlantic and Pacific oceans, whereas the distribution of Chilomycterus is highly asymmetrical with only one species in the Pacific. It seems that Diodon was as abundant in the Caribbean/Western Atlantic during the Miocene as it is there today. We analyze the paleogeographic distribution of the porcupinefishes group in Tropical America, after the complete exhumation of the Panamanian isthmus during the Pliocene.