Ground-penetrating radar (GPR) has become one of the key technologies in subsurface sensing and, in general, in nondestructive testing (NDT), since it is able to detect both metallic and nonmetallic targets. GPR has proven its ability to work in electromagnetic frequency range for subsoil investigations, and it is a risk-reduction strategy for surveying underground various targets and their identification and detection. This paper presents the results of a case study which exceeds the laboratory level being realized in the field in a real case where the scanning conditions are much more difficult using GPR signals for detecting and assessing underground drainage metallic pipes which cross an area with large buildings parallel to the riverbed. The two urban drainage pipes are detected based on GPR imaging. This provides an approximation of their location and depth which are convenient to find from the reconstructed profiles of both simulated and practical GPR signals. The processing of data recorded with GPR tools requires appropriate software for this type of measurement to detect between different reflections at multiple interfaces located at different depths below the surface. In addition to the radargrams recorded and processed with the software corresponding to a GPR device, the paper contains significant results obtained using techniques and algorithms of the processing and post-processing of the signals (background removal and migration) that gave us the opportunity to estimate the location, depth, and profile of pipes, placed into a concrete duct bank, under a structure with different layers, including pavement, with good accuracy.