Western armies, while traditionally avoiding urban combat, cannot ignore cities due to their significant operational, strategic, and political resources. This study has a dual purpose: firstly, to assess the applicability of Alice Hill's theory to a close-to-peer conflict, and secondly, to deepen understanding of the factors influencing tactical outcomes in urban warfare. Conducted as a comparative case study, it analyzes Russia's assault on Grozny and Israel's assault on Bint Jbeil. Key findings indicate that the application of Hill's tenets significantly increases the likelihood of success in such conflicts. Crucially, training and prior combat experience are shown to be decisive in determining outcomes. The study not only reinforces the validity of Hill's theory but also contributes to military professionalism by emphasizing the importance of a robust foundation for tactical success in urban areas before conflicts arise.