What does the study of the exercise of judicial discretion by judges reveal about advancing gender through adjudication? In this chapter, the author claims that, in jurisdictions of the Global South, this question cannot be limited to a study of judges or of the exercise of discretion. The focus must extend beyond the study of individual judges and/or their judgments to a study of the system of adjudication, that is to say, the laws, legal institutions and the legal and political culture within which they operate. Nine different emblematic cases involving gender justice that came before Sri Lankan courts are studied. Some of these cases were adjudicated upon by women judges while some were not. The author read the selected jurisprudence from this lens to explain advances and retreats from gender justice in adjudication. She argues that unlike in the Global North, posing the woman question of judges in the Global South, led to misleading answers regarding women’s inclusion and representation in adjudication. The analysis suggests that any link between women judges and gender justice is tenuous. The ways in which the system of adjudication operates, that is the legal institutions, the law and the legal and political culture within which disputes are resolved, better explains the possibilities and limits of gender justice in adjudication.