Ancient Rome’s medical practices have been extensively studied in the modern historical context and have provided fundamental knowledge about the history of healthcare ever since. The study uses an innovative approach of employing Artificial Intelligence and specifically Natural Language Processing to analyze the Latin medical text corpus. Since many historical studies are conducted based on qualitative textual interpretation, it aims to provide additional data and eliminate the most common limitations of processing the information about ancient medicine. The research results demonstrate qualitative findings about several most indicative aspects of Roman healthcare. Particularly, the writings reveal an evident increase in the number of Greek terms applied in the medical texts over time, thus indicating that Ancient Roman medicine began borrowing Greek practices after adopting Roman terminology. Naturally, surgery, public hygiene, and use of natural medicinal elements—herbs and vegetables—denote a versatile application of the health maintenance approaches. Moreover, the study shows that, like many issues discussed in the Roman medicine journals, ethical norms are relevant to the modern medical environment, such as confidentiality of patient information, informed consent, and referring to the professional association for controversial decisions. In terms of quantitative findings, the research indicates that the use of AI allows measuring frequency and co-occurrence of certain terms and creating timelines of their use in medical texts. Specifically, the indigenous medical practices focused on herbs, while the imported ones focused on better not drinking and eating according to the regulations.