This paper examines the permanent dentition of sixty-one individuals from the Pontokomi-Vrysi Roman rural population of the Provincia Macedonia (1st-4th c. CE) aiming to explore differences in the oral health between males and females of the assemblage. All teeth were macroscopically examined for dental pathologies and dental wear, and observations were compared at an intra-assemblage level, between males and females, as well as against published data from two Roman-Italian and two Graeco-Roman sites. Results show a homogenous pattern in the oral health of the Pontokomi-Vrysi population, pointing to a rather undifferentiated diet between the two sexes, characterized mainly by the consumption of carbohydrates and to a lesser extent by the supplementary intake of protein-deriving food sources. Comparison of the results with those from the other Greek and Italian sites reveals complex oral health and dietary profiles for these populations. This paper suggests caution when universal oral health and dietary patterns for the inhabitants of the Roman Empire are sought.