Cimolodontan multituberculates were a diverse and long-lived group of mammals characterized by large, blade-like lower fourth premolars (p4). Blade-like (plagiaulacoid) dentitions have evolved numerous times in distantly related mammalian lineages. Here we investigate how p4-shape disparity changed through time in the Cimolodonta. We address two hypotheses: (H₁) blade-like dentitions constrain the ability of plagiaulacoid mammals to evolve novel dental morphologies, (H₂) cimolodontan dental evolution proceeded gradually along a morphocline during the Late Cretaceous. We quantify functionally important aspects of p4 shape, including ratios reflecting height (H:L), symmetry (L1:L), and mesial-face height (H1:H), in a large sample of cimolodontans spanning the mid-Cretaceous through early Paleogene of North America (ca. 100–35 Mya). Our results do not support the morphocline hypothesis (H₂) and, instead, show that cimolodontans evolved a wide range of p4 shapes by the mid-Cretaceous, and that p4-shape disparity remained stable through the Late Cretaceous. We hypothesize that the two-stage cimolodontan chewing cycle (slicing-crushing then grinding) imposed functional constraints on p4 morphology. After the Cretaceous-Paleogene boundary, p4-shape disparity increased sharply, driven by the appearance of the Taeniolabidoidea, Microcosmodontidae, and Eucosmodontidae, in the early Paleocene. We contend that the slicing-crushing functions of the p4 became less important in those taxa, relaxing functional constraints on p4 morphology. Cimolodontans that retained both the slicing-crushing and grinding function of the p4 had a more limited range of p4 morphologies, and probably were largely restricted to animal-dominated omnivory. Taxa that shifted the initial slicing-crushing function from the p4 to the incisors had fewer functional constraints on p4 morphology, and were able to increase their molar grinding capacity to exploit plant-dominated omnivory and herbivory. That the p4 was reduced in herbivorous taxa rather than modified into a broader, multi-cusped tooth lends support to the morphological constraint hypothesis (H₁), and this relationship between p4 morphology and function suggests that retaining a large, blade-like p4 might have limited the range of herbivorous diets cimolodontans could exploit. These findings highlight the ecological and evolutionary limitations that specialized dentitions can impose on mammals by restricting their morphological and, in turn, functional diversification.