Through past decades of research, water has been acknowledged as one of the main parameters influencing the long-term performance of flexible pavements. The effect of water is a factor considered when designing structural and geometrical pavements. However, it unavoidably infiltrates pavement layered structures through various mechanisms. As a result, additional drainage layers, such as geocomposites, are considered among the solutions available to manage excess water in flexible pavement structures. This paper presents the analysis of drainage and structural behaviour of full scale experimental pavements built with various geocomposite drainage configurations. The tests were conducted at an outdoor research facility, the Laval University Experimental Pavement Site. Following an increase of the water table in controlled drainage conditions, the drainage and structural response of the experimental pavement sections were measured using volumetric water content transducers and a falling weight deflectometer during ten days. The overall results suggest that a lateral vertical drain is the best performing drainage configuration. Nevertheless, several observations on the effect of various drainage configurations according to their transversal and vertical position in the pavement were made using the collected experimental data.