Ear diseases, especially external auditory canal (EAC) disorders, are rarely reported in paleopathology. This study reports on the archaeological skeletal remains of two adults from the medieval period in China that presented with bony destruction in the external auditory canal (EAC). The observed pathological changes were evaluated macroscopic and microscopic, and micro-CT (micro-computed tomography) was used to examine the extent of lesion involvement. The lesions in Case 1 involved the EAC and mastoid process with smooth and regular margins. We, therefore, concluded that EAC cholesteatoma is the most likely diagnosis. In Case 2, the lesion was in the superior and posterior walls of the EAC as well as in the mastoid air cells. In this case, we arrive at the diagnosis of EAC infection. Furthermore, the potential impact of these ear diseases has been discussed. This report addresses the lack of detailed descriptions of EAC diseases in previous paleopathological publications and emphasizes the fact that the diagnosis of ear diseases in this context requires comprehensive observations of lesions as well as of all adjacent structures.