Cross‐border networks of actors constitute a special type of cross‐border cooperation as well as a special kind of network. This form of cooperation is characterized by a high degree of uncertainty, particularly in the case of the Polish‐German and the Czech‐German borders with their problematic history and rather weak traditions of cooperation. Evaluations can help to raise the effectiveness of cross‐border networks. This article refers to the concept of systemic evaluation. Such an evaluation is a collective process of learning and deliberation which is intended to increase the problem‐solving capacity of the system and to involve the participants and users from the beginning of the process. The main question dealt with in this article is how systemic evaluations of cross‐border networks of actors have to be designed and implemented. In the article, a brief survey on the state of art of systemic, participatory cross‐border evaluation is supplemented by a case study of the evaluation of the project Enlarge‐Net. The conclusions include the findings that systemic evaluations cannot be regarded separately from the intervention logic and that evaluators who are dealing with systemic evaluations of cross‐border networks of actors need a diverse tool box and have to adapt their methods to the actual phase of the cooperation.