The chapter concerns the implementation assessment of cross-border projects supported by the INTERREG VA Poland - Slovakia 2014-2020 Program. The authors diagnosed the state of implementation of the Program (2018), and analyzed the conditions for managing cross-border projects on the Polish-Slovak borderland. The chapter outlines the role of a cross-border project in management of borderland development, and presents the life cycle of a cross-border project. The authors drew special attention to the results of projects and the administrative burden related to their implementation. The authors carried out quantitative and qualitative research with the participation of Polish and Slovak beneficiaries of the Program to achieve the objectives of the work. The research was supplemented by the desk research analysis covering the selected documents and statistical data (2014 – 2018). The conclusions and recommendations can be useful in the process of programming rules for implementing cross-border projects on the Polish-Slovak borderland and other borderlands after 2020.