Eighteen late medieval central Italian paintings featuring the figure of Eve reclining on the ground beneath the enthroned Virgin have been the center of a decades-long debate among scholars. The dispute centers on whether the imagery depicts Mary as Eve's counterpart in the role of virgin mother or intercessor as the Second Eve. I argue that these two possibilities are not mutually exclusive and instead support one another. I maintain that Eve and Mary appear as opposites according to their contrasting sexual statuses because their antithesis lies at the center of the theology of the Second Eve and the heart of the signification of these paintings. Though frequently overlooked, my exploration of this imagery begins with the attributes used to identify Eve: the woman-headed serpent, the fig, and clothing. Specifically, I analyze the relationship between the particular attributes employed and the theological interpretation of the Fall as a result of concupiscent sexual intercourse. My study then turns to the individual imagery of the central figure of Mary and its reference to church teachings. Appearing amidst allusions to the Annunciation and with emblems of her roles as mother and queen, the Marian imagery in these eighteen paintings specifically reiterates the dogma of her perpetual virginity. I conclude my investigation with a discussion of how the attributes and imagery examined in the first two chapters relate to the theology of the Second Eve and provide a fundamental meaning for all medieval audiences. In light of the references to these women's sexual statuses, the imagery of the Second Eve suggests that Mary is the special advocate of men and women, religious and lay.