Roman board games such as Ludus Latrunculorum and Duodecim Scripta are among the best-documented games from the ancient world. A considerable amount of information has come down to us about social attitudes towards games, the settings in which people played, and some information about the rules of how to play games. Nevertheless, there is much that remains unclear about the games of Ancient Rome because they have largely been ignored in scholarship. This talk explores the archaeology of ancient Roman play through traditional archaeological methods and targeted AI-simulated play to expand our knowledge of Roman games. It highlights the work of the upcoming project Play and the City: Investigating the Cultural Heritage of Games of the City of Rome to accurately document graffiti games in the urban environment of Rome itself, while also exploring the ways that AI has been used to identify the games played on particular boards found at Roman sites. It will also highlight the intersection of these two projects as manifested through the GameTable COST Action.