Teleost tooth replacement is historically categorized into two discrete modes: replacement occurring in soft tissue outside the dentigerous bone (extraosseous) or within dentigerous bone (intraosseous). However, increasing evidence suggests more complexity. Extraosseous is considered the plesiomorphic state in teleosts and intraosseous derived, although there appear to be reversals to the plesiomorphic state in some taxa. The combtooth blennies are characterized by a heterodont dentition consisting of a single row of anteriorly positioned feeding teeth and posteriorly located canines that can be present on both the upper and lower jaws. However, no studies have investigated canine replacement or its relation to feeding tooth replacement in blennies. We used methods including histology, clearing & staining, and micro-CT to explore the question: Is canine replacement developmentally distinct from feeding tooth replacement in blennies? We found that canines are always replaced intraosseously, while feeding teeth range across taxa from extra- to intraosseous replacement. Following the observation of taxa that simultaneously possess intraosseous canine replacement and extraosseous feeding tooth replacement, we hypothesize that extraosseous replacement is derived from intraosseous replacement in blennies. Preliminary results from phylogenetic comparative analyses support our hypothesis, indicating that many blennies possess a derived extraosseous replacement mode. Teleost tooth replacement is far more complex than current categories suggest. Re-thinking categorizations to be inclusive of taxa with complex dentitions may provide valuable insight into processes related to the evolution of trophic morphological novelties in teleost fishes.