Based on interviews with party leaders and Members of the Scottish Parliament, this paper examines the pathways to party leader position in four parties in Scotland: the Conservative and Unionist Party, the Green Party, the Labour Party, and the Scottish National Party. The paper examines leader selection structures to assess which might facilitate (or impede) women’s leadership candidacies, and it hypothesizes that women will have their best opportunities for access to leadership in low-competition contexts related to electoral or political crisis and defeat. The paper argues that party leadership contests are identifiably gendered in structure and competitive process, and concludes with speculations about the generalizability of the Scottish case to party leader contests at the national level.