Trepanation is one of the most ancient and applied surgical treatments; several archaeologically documented cases are known, dated back from prehistory to the Middle Ages. This case study reports the anthropologic analysis of the skeletal remains of a young medieval woman and a fetus (Imola, Italy). The fetal remains were laid between her pelvis and lower limbs. A perforating injury was observed to her frontal bone. After assessing biologic profiles, we attempted to interpret the injury and to reconstruct possible circumstances of death. The lesion seems commensurate with a surgical intervention; signs of an osteogenic reaction were detected at its edges. It can be hypothesized that the survival of the woman undergoing the surgery was approximately 1 week and the fetus extruded after the burial. Thus, this case represents a unicum, spreading more light on the history of neurosurgery during the Early Middle Ages in Europe.