The skeletons investigated herein were dated to the Late Eastern Roman Period, at the time of the golden age under the reign of the Macedonian dynasty ruled between 867 and 1056. In the Kütahya region, which acted as a border and frequently changed between the Eastern Roman and Seljuk states, the oral and dental health of the Attepe and Dereköy populations in this period was differed proportionally. A dam was constructed in Kütahya Province near Kureyşler Village for irrigation purposes. The Attepe settlement (AD 986-1050) and Dereköy necropolis (AD 966-1032) are located within the boundaries of the dam lake. To save the cultural assets in these areas, excavation studies were conducted by the Kütahya Museum in the region in 2014. This study investigated 447 permanent teeth from 34 adult individuals in the Attepe population, and 270 permanent teeth from 17 adult individuals in the Dereköy population dated to the Late Eastern Roman period. When the distribution of dental diseases in the Attepe population was examined, it was determined that 13.77% had caries, 0.81% had periapical lesions, 68.18% had periodontal disease, 13.07% had calculus, 17.98% had hypoplasia, and 22.33% had antemortem tooth loss (AMTL). In the Dereköy population, 12.88% had caries, 2.01% had periapical lesions, 80% had periodontal disease, 3.83% had calculus, 23.28% had hypoplasia, and 5.37% had AMTL. In both populations, the degree of tooth wear was determined as grade 3 and 4. The dental data showed that agricultural-dominated nutrition consumption was effective in the Attepe and Dereköy populations. In both populations, there were significant differences between the amount of caries and calculus (p = 0.00 < 0.05) as well as tooth wear and calculus (p = 0.00 < 0.05). When all these findings were assessed in an integrated fashion, it was possible to understand the features of a village population being involved in agriculture and dominant stock farming in a region in western Anatolia during the 10th-11th centuries, which coped, for the most part, with epidemics and infectious diseases, wars, and perhaps periodic famines.