A complex cylindrical structure consisting of a group of parallel stratified circular lossy dielectric cylinders, embedded in a dielectric circular cylindrical region and surrounded by unbounded dielectric space, is considered in this paper. The scattering of electromagnetic (EM) plane waves by the aforementioned configuration was studied; the EM waves impinged obliquely upon the structure and were arbitrarily polarized. The formulation used was based on the boundary-value approach coupled with the generalized separation of variables method. The EM field in each region of space was expanded in cylindrical wave-functions. Furthermore, the translational addition theorem of these functions was applied in order to match the EM field components on any cylindrical interface and enforce the boundary conditions. The end result of the analysis is an infinite set of linear algebraic equations with the wave amplitudes as unknowns. The system is solved by the truncation of series and unknowns and then matrix inversion; thus, we provide a semi-analytical solution for the scattered far-field and, as a consequence, for the scattering cross section of the complex cylindrical structure. The numerical results focus on calculations of the electric- and magnetic-field intensity of the far-field as well as of the total scattering cross section of several geometric configurations that fall within the aforementioned general structure. The effect of the geometrical and electrical characteristics of the structure on the scattered field was investigated. Specifically, the cylinders’ size and spacing, their conductivity and permittivity as well as the incidence direction were modified in order to probe how these variations are imprinted on scattering. Moreover, comparisons with previously published results, as well as convergence tests, were performed; all tests and comparisons proved to be successful.