Bioarchaeological studies have found that, in general, the adoption of agriculture is associated with deteriorating oral health, most frequently manifested as an increase in the prevalence of dental caries. However, compared to other regions of the world, bioarchaeological studies focusing on prehistoric Europe have produced more variable results, with different populations experiencing deteriorations, improvements, and stasis in oral health. This study assesses the oral health of individuals of the Tripolye culture buried in Verteba Cave, Ukraine, within the context of the transition to agriculture in Eastern Europe. We compare the rates of dental caries between Tripolye farmers with earlier hunter-fisher-gatherers from Ukraine. The Tripolye were found to have carious lesions on 9.5 per cent of teeth, while the hunter-fisher-gatherers were found to be universally free of carious lesions. A Fisher's exact test demonstrates that this difference is statistically significant, supporting the model that the transition to agriculture was detrimental to oral health in prehistoric Ukraine. This could be related to the manner in which grain was processed by the Tripolye and the needs of their relatively population-dense society.