The concept of truck platooning is to take advantage of the connectivity technologies and automated driving support systems to link trucks in close formation (convoy) to increase transport efficiency, reduce fuel consumption and gas emissions while improving road safety. However, closely following guided trucks could have a different impact on road structures than the usual truck traffic. In this context, the study reported in this paper addresses the multi-loading effects of truck platoons on road structures. For this purpose, an experimental test track located in Spain was instrumented with longitudinal and transversal strain gauges. The strain gauges were used to collect the strains obtained in the pavement under the following conditions: (1) trucks in individual and platoon configuration, (2) a time gap of 0.8 s between trucks in the platoon configuration, and (3) four speeds (40 km/h, 60 km/h, 70 km/h and 80 km/h). The viscoelastic response of the pavement structure (strain field) under the test conditions applied on-site was computed using software Viscoroute 2.0 and was compared with the results measured with the strain gauges. Finally, the effect of individual and platoon truck configurations was compared.