This paper examines the influence of reproducing the stress history of Hawthorn Group (HG) clays during laboratory reconsolidation on the subsequent shear stiffness degradation response under compression paths. Thin-walled Shelby tube samples of lightly overconsolidated HG clays were extracted from the Deep Foundation Test Site at the University of Central Florida Arboretum. Undrained triaxial compression tests with local instrumentation, bender elements, and Hall effect transducers, were performed to capture strains at different levels. Soil response is compared with a conventional laboratory technique where specimens are anisotropically consolidated to the in situ stress state, and no stress history of the soil deposit is reproduced. Results are evaluated in terms of stress-strain-strength responses with emphasis on shear stiffness degradation. Significant differences on the onset of shear stiffness degradation were observed for θ-values approaching 180° in concordance with the stress path rotation angle concept. Reproducing the stress history of HG clays impacts the stiffness at small strains whereas no significant differences were observed in the undrained shear strength of the material.