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The detection and analysis of tree roots in urban environments are becoming more and more important for mitigating structural damage caused by root expansion under pavement. Ground-penetrating radar (GPR) is a valuable tool for non-destructive subsurface investigations. This study presents an application of GPR to detect tree roots under various pavement types and different urban environments in Portugal, incorporating experimental data and synthetic modelling using GPRMax. Field measurements were conducted at multiple urban locations with diverse surface conditions, including concrete, asphalt, and cobblestone. Results indicate that pavement materials significantly affect GPR signal penetration and root detectability. Synthetic modelling in GPRMax was performed to simulate radar responses for different root systems and validate field observations. The findings contribute to improving tree root detection techniques in urban settings and optimizing geophysical survey parameters.