Mammals inhabit all types of environments and have evolved chewing systems capable of processing a huge variety of structurally diverse food components. Surface textures of cheek teeth should thus reflect the mechanisms of wear as well as the functional traits involved. We employed surface textures parameters from ISO/DIS 25178 and scale-sensitive fractal analysis (SSFA) to quantify dental wear in herbivorous mammals at the level of an individual wear enamel facet. We evaluated cheek dentitions of two grazing ungulates: the Blue Wildebeest (Connochaetes taurinus) and the Grevy's Zebra (Equus grevyi). Both inhabit the east African grassland savanna habitat, but they belong to fundamentally different taxonomic units. We tested the hypothesis that the foregut fermenting wildebeest and the hindgut fermenting zebra show functional traits in their dentitions that relate to their specific mode of food-composition processing and digestion. In general, surface texture parameters from SSFA as well as ISO/DIS 25178 indicated that individual enamel ridges acting as crushing blades and individual wear facets of upper cheek teeth are significantly different in surface textures in the zebra when compared with the wildebeest. We interpreted the complexity and anisotropy signals to be clearly related to the brittle, dry grass component in the diet of the zebra, unlike the wildebeest, which ingests a more heterogeneous diet including fresh grass and herbs. Thus, SSFA and ISO parameters allow distinctions within the subtle dietary strategies that evolved in herbivorous ungulates with fundamentally different systematic affinities but which exploit a similar dietary niche. SCANNING 32: 162–182, 2010. © 2010 Wiley Periodicals, Inc.