Abstract Unassociated human bones are a particular problem during the exhumation of mass graves and a factor that limits anthropological and paleopathological analyses from archaeological contexts. Extensive anthropological literature has focused on the complex taphonomic factors that influences bone assemblages, but little attention has been paid to postmortem tooth loss and factors affecting this process. The following study focuses upon the influence of different factors on postmortem tooth loss. Three samples were investigated in the study: a medieval church cemetery containing 110 individual skeletal remains, and two samples from a series of mass graves made within the same time period in 1999, containing 402 bodies. The frequency of postmortem tooth loss was analyzed relative to postmortem interval for each sample, excavation methods, age distribution, and presence of bone loss associated with periodontal disease. Our results indicate that the degree of alveolar bone loss significantly affected both antemortem and postmortem tooth loss and that the frequency of postmortem tooth loss has the strongest correlation to time since death. These findings suggest that additional care should be taken when exhuming remains from older contexts.