The capacity to produce multiple generations of teeth allows for changes in dentition morphology throughout an animal's life. This adaptation can accommodate different dietary strategies at different life stages, most notably between juvenile and adult stages. Common changes between tooth generations include variations in tooth number and morphological parameters. In this study, we compare the dentition morphology of juvenile and adult specimens from four species of Cuban false chameleons in the genus Anolis (Chamaeleolis group) within the Iguania clade of squamate reptiles. Unlike most anole lizards, which are primarily insectivorous or saurivorous, these species are specialised feeders on shelled snails and possess distinctive broad molariform teeth at the back of their jaws. The exact dietary preferences of these species remain unclear. Our findings reveal that juveniles differ from adults by the presence of tricuspid teeth at the back of the jaw and that the examined species exhibit differences in dentition, such as tooth number, shape, arrangement of cusps and crests, presence of molariform teeth, and internal tooth structure. Based on these observations, we discuss how interspecific and age-related changes in dentition may reflect differences in diet.