First, the paper presents the position of the ICT sector in the Czech Republic (CZ) as a transition economy; it pays particular attention to the ICT industry, university studies, research, and development. Then, it focuses on academic-industrial cooperation (AIC) in the CZ. As economic conditions in the CZ are different from the traditional developed economies, the AIC might not necessarily exhibit the same characteristics. Thus, the paper tries to identify potential differences on two concrete cases of two schools (faculties) at two Czech universities. The research is based on interviews with companies and stakeholders from the participating faculties. In comparison with the findings known from the literature on this issue in developed countries, the interviews revealed some differences such as a more positive attitude toward engagement of academicians in private companies and further education at universities. Specific local issues have been discovered such as small volumes of cooperation, not enough flexible researchers, and lacking business orientation at the universities.