This paper analyzes the role of women in various types of transnational organized crime and tests the ‘gendered markets’ hypothesis by Zhang et al. (Criminology 45(3):699–733 2007) for a wide cross-section of 150 cases from the Dutch Organized Crime Monitor. The main information sources for the Dutch Organized Crime Monitor are closed Dutch police investigations into criminal groups, often spanning a period of several years. Following four data sweeps, a wide cross-section of 150 cases was collected about various forms of organized crime (period 1994–2011): ‘traditional’ drug trafficking cases (cocaine, heroin, and cannabis), but also other—less frequently prioritized—phenomena such as synthetic drugs (production and export), human smuggling, human trafficking, and fraud and money laundering. The paper discusses several important theoretical perspectives from the organized crime literature: the gendered markets hypothesis; the social embeddedness of (transnational) organized crime: and the idea of brokerage. Furthermore, empirical data are presented on how often women play a (prominent) role in different types of criminal activities and which roles they play. These findings are related to the ‘gendered markets’ hypothesis and alternative explanations. Further qualitative analysis is presented on the transnational aspects which can be discerned in the studied cases: transnational marriage and transnational relationships; language and mediation; and migration and legal status. Finally, the main conclusions are discussed as well as their theoretical and empirical relevance.