The use of Electric Vehicles (EV) seems to be a promising solution to achieve a sustainable road transport system. Among the contactless dynamic vehicle charging technologies, the use of Charging Units (CUs)—cement concrete box—embedded into the road pavement seems to be a favorable option. The available scientific papers related to the structural effects of embedding CUs in road pavements consider the CU as a solid box, even if a cavity is needed for the electrical technologies’ accommodation. This is why the current research is aimed at studying electrified roads (e-road) with different CU cavity shapes and dimensions. In detail, pavement structural responses are investigated, as a first step, adopting a Finite Element Model (FEM), and, as a second step, the long-term performances (fatigue cracking/rutting proneness) are evaluated. The study is divided into two phases: the theoretical fatigue/rutting assessment, which allows to calculate the critical load repetitions leading to pavement failure, and an urban case study with the goals of both assessing the theoretical results and computing fatigue/rutting performance with real scale traffic conditions. The outcomes demonstrate that CUs can be used with no significant impacts on the long-term road pavement structural performance, laying the foundation for a future upgrading of the existing urban road networks.