All agri‐food cooperatives share common interests, irrespective of their geographical borders, which should encourage them to undertake inter‐cooperation processes as well as to set up transnational cooperatives. This paper has two objectives. The first is to analyze Spanish and Portuguese cooperative regulations and the Statute for a European Cooperative Society to define how to embark on these processes in the two countries while also pinpointing the conflicts that may arise from the different regulations. Secondly, it seeks to ascertain which Spanish and Portuguese cooperatives have had experience in this field and to characterize them through a multiple‐case study, including the rationale for the processes, the advantages and the constraints. The results have revealed five cross‐border cooperation categories and show that the Statute for a European Cooperative Society has not had the expected success at the EU level, due to its complexity. However, in general, the lack of expected cross‐border cooperative experiences is not due to legal, language or management issues. It is for different reasons. Firstly, cooperatives think that they can achieve the same objectives through inter‐cooperative agreements. Secondly, government policies protect the regional nature of their cooperatives, rather than encouraging them to expand their business and therefore their capacity to respond to current challenges.