In the area of smart cities, great emphasis is placed on many different fields such as energetics, information systems, and transportation. All of these should lead to a simplification of life thanks to smart technologies. If we talk about the transportation field, the main issues related to this area are safety, traffic efficiency, or the environment. Another condition is the successful acceptance of any new technology by its users. Cooperative systems prove to be a suitable solution for these issues, especially in urban areas. Today, pilot implementations of cooperative systems in European countries are being carried out. However, before they are put into full operation, they need to be tested, evaluated, and assessed. This article focuses on the latter two points, i.e., evaluation and assessment of the cooperative systems. For this purpose, a methodology was created, which describes the procedure chosen in the evaluation and assessment of cooperative systems in the Czech Republic and a demonstration of its use by example. The methodology is focused on three main areas, which in this case are functional evaluation, user acceptance, and impact assessment. For the area of user acceptance, the main source was questionnaires, impact assessment relied on measured data while functional evaluation was based on discussions with the drivers, evaluating the cooperative systems, the measured data, and the expert observations. All collected and measured data were then processed and some of the results of the evaluation of the selected service are presented at the end of this article.