Different constitutive models, based on principles of mechanics and experimental evidence, have been developed over several decades to represent and predict the stress-strain behavior of soils subjected to various loading conditions. The Generalized Bounding Surface Model (GBSM) is one of them and is defined as a fully three-dimensional elastoplastic constitutive model for saturated cohesive soils that employ the bounding surface plasticity in conjunction with a nonassociative flow rule and a soil microfabric-inspired rotational hardening rule. The GBSM has been successfully validated on numerous laboratory reconstituted soils, but not on natural or undisturbed soil samples. Hence, in this paper the predictive capabilities of the GBSM are evaluated in the simulation of the monotonic behavior of an undisturbed cohesive soil called “Cajicá clay” from the high plain of Bogotá in Colombia. In the first instance, an isotropic consolidation test and a set of axisymmetric triaxial compression and extension tests are conducted using an automated triaxial equipment, to experimentally describe the response of the undisturbed soil. From experimental data, the parameters associated with the GBSM model are calibrated to finally evaluate its capabilities in the simulation of a cohesive natural soil. A comparison between experimental data and numerical simulations is presented to show both performance and advantages of the GBSM model.