The Europeanization of gender equality policies in times of economic crisis reveals conflicting dynamics. While EU gender equality policies promote equality in its member states, EU and member states’ austerity policies spur cuts in public budgets and deregulatory employment policies that endanger gender equality. We explore these paradoxical Europeanization dynamics by studying discursive and material resistances and opportunities encountered in the implementation of gender equality policies in Spanish judicial litigation. We will analyze three court cases in the area of equal employment (Elbal Moreno, García Mateos and Roca Álvarez) in their different stages before Spanish and supranational courts (Court of Justice of the European Union and European Court of Human Rights). By comparing different judicial decisions at national and supranational levels we aim at unraveling the discursive and material resistances and opportunities that appear when putting gender equality policies in practice in multilevel contexts. EU and Spain’s austerity politics intervened in a context, such as the Spanish, in which gender equality policies are strongly institutionalized, but still weakly implemented in the judicial system. We argue that the discourse of austerity offered the Spanish courts arguments to convey in a new way old resistances and oppositions, while the opportunities offered by the EU legal context have not yet been fully incorporated in Spanish judicial decisions. We are interested in exploring how these “new” resistances emerging in the context of austerity interact with the “old” forms of machismo articulated by Spanish gendered courts. The analysis of individual agency, judicial structures and discourses, through the critical frame analysis of judicial documents and interviews with claimants, lawyers, and judges, will allow us to understand the emergence and persistence of oppositions and opportunities for Europeanizing gender equality in Spain’s austerity context.