This article aims to analyse gender roles and the position of women in the judiciary in medieval Serbia, focusing on sex and gender in all the key roles in the judiciary: witnesses and jurors, parties and judges. The sources present a somewhat conflicting picture. While only men could occupy official positions appointed by the State, feudal lords possessed the right to judge the tenants of their lands, and thus widowed noblewomen might have acted as judges in such a role. Regarding women as parties in court, the Law Code of Emperor Dušan (1349) proclaims that a poor widow who could not stand trial on her own has the right to appoint her representative. Does this mean that a woman was not allowed to appear as a party in court without a man representing her—or is it merely a beneficial socially motivated norm aimed at only those women who would have practical problems with presenting their case in court? A norm transplanted from Byzantine law in the fourteenth century limits the testimony of women exclusively to feminine matters. However, there is evidence of a woman witness in a late twelfth century heresy case—and before the Sabor (Parliament), no less—and women also appear as witnesses in documents from the late fourteenth century. Were the rights of women as witnesses subsequently limited, making the preserved early case a political exception, or was the transplanted limitation ignored in practice? Finally, a norm from the same Code clearly shows that both men and women could be jurors—but this sex-specific formulation is not consistently present in all manuscripts. I shall attempt to address all these complexities -and some other dilemmas- and present a nuanced picture of the gender (im)balance before the courts of medieval Serbia.