Late Wordian/Capitanian (Guadalupian, Middle Permian) fish assemblages are described from the “McKittrick Canyon Limestone”, Lamar Limestone and Reef Trail Members of the Bell Canyon Formation in the Patterson Hills and the PI section (Hegler/Pinery Members) along Highway 62/180 in the Guadalupe Mountains, West Texas. The assemblages contain chondrichthyan teeth of Stethacanthulus meccaensis, Texasodus varidentatus, Cooleyella cf. amazonensis, C. cf. peculiaris, and the new genus and species Lamarodus triangulus; and buccopharyngeal denticles of undetermined symmoriiform; chondrichthyan scales of eight morphotypes; fragment of an actinopterygian jaw, isolated teeth; the scales of Alilepis sp., Varialepis sp. and undetermined elonichthyid and haplolepid fishes. Using microtomography, the vascularization system has been observed for the first time for the teeth of Texasodus varidentatus and a new taxon Lamarodus triangulus. The distribution of chondrichthyan taxa was analyzed for the known fish assemblages of the Early, Middle, and Late Permian of the world. The end-Guadalupian crisis in the evolution of chondrichthyan fishes involved substantially more taxonomic change than the Permian–Triassic mass extinction.