Plasticity of tooth shape in mammals is of great adaptive value for the efficient exploitation of specific feeding niches and is a crucial mechanism for ecological diversification. In this study, we aimed to infer chewing effectiveness from the functional shape of different postcanine teeth within bovids, the most diverse extant group of large herbivorous mammals. We consider the postcanine dentition as a masticatory unit and test for differences related to food biomechanical properties, dietary abrasiveness, and chewing dynamics. We compare functional properties of the postcanine tooth row among species with well-known dietary strategies by integrating digitalization of high-resolution occlusal surface 3D-models of upper postcanine dentitions and quantification of the indentation index (D), a structural parameter representing enamel complexity. We test for differences in the occlusal shape among tooth positions in the postcanine dentition using robust, heteroscedastic tests in a one-way analysis of variance. Our results show three distinct patterns of enamel complexity along the tooth row: (1) D is more homogeneously distributed among tooth positions; (2) D increases gradually in the mesiodistal axis along the tooth row; and (3) D increases abruptly only at the transition between premolars and molars. We interpreted these patterns as different adaptive configurations of the postcanine tooth row relating to diet. Grass- and fruit-eating bovids show the same abrupt increase in enamel complexity at the transition from premolars to molars. Intermediate feeding and leaf-browsing species show the same gradual, mesiodistal increase in complexity along the tooth row. The absolute physical dietary resistance (biomechanical properties plus abrasiveness) and its relation to mechanical constraints of the chewing stroke are the likely selective factors leading to convergence of enamel complexity patterns along the tooth row among taxa with different diets. J. Morphol. 275:328–341, 2014. © 2013 Wiley Periodicals, Inc.