With a world than is becoming more and more urbanized and with more importance being placed on cities the likelihood that our urban centers will be the focus of future warfare increases. This study will examine how Alice Hills theory can explain success in urban warfare in a comparative case study. The purpose of this study is to affect the validity of Hills theory. This method used in this study is a theory testing case to examine to what extent Hills´s theory can explain the failure during the first battle of Grozny and the success during the second battle of Grozny and by doing so increasing the validity of hills Theory. The two cases have similar background variables, which allows for a structured comparison of the two cases. The analysis is based on Hills’s success factors in urban warfare. The results show the importance of morale and skill in urban combat.