In modern populations, inequalities in oral health have been observed between urban and rural communities, but to date the impact of the place of residence on oral health in archaeological populations has received only limited attention. This meta-study analyses dental palaeopathological data to examine the relationship between place of residence and oral health in Roman, early medieval, and late medieval Britain. Published data on ante-mortem tooth loss, calculus, caries, dental abscesses, and periodontal disease were analysed from cemeteries in urban and rural locations from each period. The results indicate that the place of residence influenced oral health in Roman and late medieval times, with urban populations enjoying better oral health than rural populations in Roman Britain, but poorer oral health in the late Middle Ages. These findings may reflect changes in the nature of urban settlements and in their relationship with their rural hinterlands over time.